Can I use a tax treaty to strip my company of assets and avoid departure tax?

[WorldCitizen99]

I just joined as a Gold Member Light
If there is a membership area to post this in, someone please let me know. I haven't gone through all the features of the membership area yet.

OK this q is longer than average - skip down to the tl;dr if u just want the abridged version. But I think it is worth reading as it highlights some issues in int'l tax planning using tax treaties.


Situation
Having a liquidated Cdn company with significant cash in it, wanting to depart the Canadian tax system and just getting money out of the company at the lowest tax rate possible. I spend most of my time OUTSIDE of Canada but I still use a Canadian address as my permanent address and I still file as Cdn tax resident. I don't meet formal criteria for any foreign jurisdiction to be considered tax resident there.


Problem
Changing tax-residency incurs a 'departure tax' of 26.7% of the fair-market value of the company (=cash value of company). So tax= $267K on 1M in cash assets. BUT that is just the cost of changing tax-residency.
One still has to pay dividend withholding tax to get the money out of the company
25% div WHT for non-treaty countries
5-15% for treaty countries

Taking all money out in one shot as a dividend prior to changing tax residency would be at 47%
Paying departure tax and taking out dividends at 15% using tax treaty = effective tax rate of 37%

Question
Can one remain Cdn tax res to avoid departure tax and set up foreign company in jurisdiction where it is considered resident of the foreign country by their local laws, e.g. US, Bulgaria, and where the tax treaty tiebreaker clause (Article 4) will say that it is tax resident of the foreign country. (I realize one might still have to pay taxes upon paying out dividends from the foreign company, depending on the jurisdiction).

If this is the case, can dividends be paid from the Cdn company to the foreign company at the reduced treaty rate?

Next Question
If the above would work, the next question becomes
'can one set things up so that the 5% rate can be achieved?'
This would require that the recipient (foreign) company already owns a portion of the (Cdn) company paying the dividends.

The only way I can imagine this would work is if a Cdn holding company with NOMINAL, e.g. $100, paid-up capital was registered, and say 25% of the shares were then sold to the foreign company and this situation was allowed to sit for a year (I think this is often a requirement).

Then the assets would be transferred to the new Cdn holding company (hopefully tax-free, otherwise not worth it). Transferring assets via a 'section 85 rollover' to a Cdn holding company requires that the company be 'Canadian' - which again brings up the requirement to have M&C inside Canada. Again, for this requirement, is filing your taxes in Canada sufficient or does one need to spend time in Canada (and not carry on business in Canada since carrying on business via a permanent establishment or as independent professional service in Canada would invalidate the 5-15% treaty rate as per "Article 10: Dividends")

Is this too good to be true and would trigger anti-avoidance measures or is this possible?

The alternative is to just keep my Cdn tax residency and let the money sit in Canada and only take out 75K/year - that would be low enough tax and would cover living expenses while letting principle grow thru investments.
However, I have seen enough from the current government that makes me want to reduce exposure to Canada in the medium and long term.
I would also forego the benefits of a better tax regime.


tl;dr
Can one be tax resident of one country and have a corporation in that same country pay out dividends at the reduced treaty rate to a company that they own in another country, assuming the local laws and tax treaty allow that company to be tax resident of that other country?

 

[Sols]

Not the answer you were hoping for but your questions are very, very specific to Canadian tax law and the only person equipped to answer them in detail is a Canadian lawyer/tax adviser.

As a general rule, actions already taken prior to relocating are taxed where they took place. If the liquidation is already done or already initiated and you (as the beneficiary of the liquidation) were resident in Canada at the time, that's all subject to Canadian tax law even if you depart right now and never return to Canada.

But as with most things tax law, there is a lot nuance.

Situation
Having a liquidated Cdn company with significant cash in it, wanting to depart the Canadian tax system and just getting money out of the company at the lowest tax rate possible. I spend most of my time OUTSIDE of Canada but I still use a Canadian address as my permanent address and I still file as Cdn tax resident. I don't meet formal criteria for any foreign jurisdiction to be considered tax resident there.

So the situation is that you have incurred an income while tax resident in Canada.

Question
Can one remain Cdn tax res to avoid departure tax and set up foreign company in jurisdiction where it is considered resident of the foreign country by their local laws, e.g. US, Bulgaria, and where the tax treaty tiebreaker clause (Article 4) will say that it is tax resident of the foreign country. (I realize one might still have to pay taxes upon paying out dividends from the foreign company, depending on the jurisdiction).

If this is the case, can dividends be paid from the Cdn company to the foreign company at the reduced treaty rate?

Yes, in principle. If the company is genuinely, bona fide tax resident somewhere else, you may be able to access treaty withholding tax rate.

Can one be tax resident of one country and have a corporation in that same country pay out dividends at the reduced treaty rate to a company that they own in another country, assuming the local laws and tax treaty allow that company to be tax resident of that other country?

This is less clear cut because the specifics of Canadian law matters. There are probably anti-avoidance mechanisms in the departure tax law.

If your plan is to sell your Canadian company to a company in Bulgaria, liquidate the company, have the Bulgarian company receive the cash from the liquidation, and then pay yourself that money, it sounds on a surface level like it would work assuming you establish yourself in Bulgaria and the company is truly and solely tax resident there. But if CRA didn't fail Tax Evasion 102, they probably planned for schemes like this.

Your idea sounds plausible but will require analysis by someone actually trained in Canadian tax law.

 

[KDX]

I just joined as a Gold Member Light
If there is a membership area to post this in, someone please let me know. I haven't gone through all the features of the membership area yet.

OK this q is longer than average - skip down to the tl;dr if u just want the abridged version. But I think it is worth reading as it highlights some issues in int'l tax planning using tax treaties.


Situation
Having a liquidated Cdn company with significant cash in it, wanting to depart the Canadian tax system and just getting money out of the company at the lowest tax rate possible. I spend most of my time OUTSIDE of Canada but I still use a Canadian address as my permanent address and I still file as Cdn tax resident. I don't meet formal criteria for any foreign jurisdiction to be considered tax resident there.


Problem
Changing tax-residency incurs a 'departure tax' of 26.7% of the fair-market value of the company (=cash value of company). So tax= $267K on 1M in cash assets. BUT that is just the cost of changing tax-residency.
One still has to pay dividend withholding tax to get the money out of the company
25% div WHT for non-treaty countries
5-15% for treaty countries

Taking all money out in one shot as a dividend prior to changing tax residency would be at 47%
Paying departure tax and taking out dividends at 15% using tax treaty = effective tax rate of 37%

Question
Can one remain Cdn tax res to avoid departure tax and set up foreign company in jurisdiction where it is considered resident of the foreign country by their local laws, e.g. US, Bulgaria, and where the tax treaty tiebreaker clause (Article 4) will say that it is tax resident of the foreign country. (I realize one might still have to pay taxes upon paying out dividends from the foreign company, depending on the jurisdiction).

If this is the case, can dividends be paid from the Cdn company to the foreign company at the reduced treaty rate?

Next Question
If the above would work, the next question becomes
'can one set things up so that the 5% rate can be achieved?'
This would require that the recipient (foreign) company already owns a portion of the (Cdn) company paying the dividends.

The only way I can imagine this would work is if a Cdn holding company with NOMINAL, e.g. $100, paid-up capital was registered, and say 25% of the shares were then sold to the foreign company and this situation was allowed to sit for a year (I think this is often a requirement).

Then the assets would be transferred to the new Cdn holding company (hopefully tax-free, otherwise not worth it). Transferring assets via a 'section 85 rollover' to a Cdn holding company requires that the company be 'Canadian' - which again brings up the requirement to have M&C inside Canada. Again, for this requirement, is filing your taxes in Canada sufficient or does one need to spend time in Canada (and not carry on business in Canada since carrying on business via a permanent establishment or as independent professional service in Canada would invalidate the 5-15% treaty rate as per "Article 10: Dividends")

Is this too good to be true and would trigger anti-avoidance measures or is this possible?

The alternative is to just keep my Cdn tax residency and let the money sit in Canada and only take out 75K/year - that would be low enough tax and would cover living expenses while letting principle grow thru investments.
However, I have seen enough from the current government that makes me want to reduce exposure to Canada in the medium and long term.
I would also forego the benefits of a better tax regime.


tl;dr
Can one be tax resident of one country and have a corporation in that same country pay out dividends at the reduced treaty rate to a company that they own in another country, assuming the local laws and tax treaty allow that company to be tax resident of that other country?

What actually determines the fair-market value of the company? what if unfortunately your company suddenly lost most of it's value? Wink-wink
On a real note, contact a tax lawyer like Sols said

 

[WorldCitizen99]

Thank u for the thoughtful and detailed answer.
Yes any final decision will have to be run by a Cdn tax expert.

It would be great to know all the jurisdictions where such a setup can occur i.e. corporate residency rules based on place of incorporation with an associated tax treaty that gives the tiebreaker to the place of incorporation also.

From watching the videos of a populat Youtuber, it seems the list includes Bulgaria, Estonia, US, Barbados and UAE but there might be others bc Armenia seems to fit the bill.

Just for the benefit of anyone in the same boat, I found this link that gives quick access to local rules by country
https://www.oecd.org/tax/automatic-exchange/crs-implementation-and-assistance/tax-residency/And the list of tax treaties for Canada - check Article 4
https://www.canada.ca/en/department-finance/programs/tax-policy/tax-treaties.html

What actually determines the fair-market value of the company? what if unfortunately your company suddenly lost most of it's value? Wink-wink
On a real note, contact a tax lawyer like Sols said

hehe
yes if I was a forward thinker, I would have scheduled an unforeseen boating mishap

 

[KDX]

It would be great to know all the jurisdictions where such a setup can occur i.e. corporate residency rules based on place of incorporation with an associated tax treaty that gives the tiebreaker to the place of incorporation also.

Look up terms like: Permanent Establishment, CRC, Place of management, I'll add more if I can remember but these will help you get an idea of how this "corporate residency" stuff works. Not sure about any specific Canada tax treaties. Usually the "based on place of incorporation" is pretty meaningless if there is another country involved

hehe
yes if I was a forward thinker, I would have scheduled an unforeseen boating mishap

I'm just thinking, if you can somehow decrease the value of the company legally e.g. by investing in a subsidiary in let's say Estonia, or loaning money to that subsidiary etc. I haven't really thought this stuff out too much but, you never know, there could be some loophole you could use to at least alleviate some of the tax burden.

 

[Sols]

It would be great to know all the jurisdictions where such a setup can occur i.e. corporate residency rules based on place of incorporation with an associated tax treaty that gives the tiebreaker to the place of incorporation also.

Corporate tax residence needs to be considered from two perspectives: where the company is incorporated and Canada.

For example, if you live in Canada and form a company in Bulgaria (where you are the shareholder/director/UBO), the company is resident in both Bulgaria (through incorporation) and Canada (through place of effective management). If your plan includes staying tax resident in Canada, this will be where your plan risks falling apart.

From watching the videos of a populat Youtuber, it seems the list includes Bulgaria, Estonia, US, Barbados and UAE but there might be others bc Armenia seems to fit the bill.

Look carefully at UAE. Because it's a zero tax jurisdiction, tax treaties usually only apply to UAE nationals. There might be similar restrictions in the treaty with Barbados since it's a low tax jurisdiction.

 

[WorldCitizen99]

Corporate tax residence needs to be considered from two perspectives: where the company is incorporated and Canada.

For example, if you live in Canada and form a company in Bulgaria (where you are the shareholder/director/UBO), the company is resident in both Bulgaria (through incorporation) and Canada (through place of effective management). If your plan includes staying tax resident in Canada, this will be where your plan risks falling apart.


Look carefully at UAE. Because it's a zero tax jurisdiction, tax treaties usually only apply to UAE nationals. There might be similar restrictions in the treaty with Barbados since it's a low tax jurisdiction.

Yes - if I understand it correctly, the Bulgarian-incorporated company would be dual resident but the tiebreaker rule in Article 4 of the treaty would rule that it is a Bulgarian tax resident. Maybe it would be prudent to build up some economic substance in Bulgaria to minimze the chance that they apply some anti-avoidance clause.

If I change my personal tax residency, I automatically get stuck with the departure tax so all I can do is try to play with corporate tax residency rules and there seem to be only a handful of jurisdictions that have treaties with Canada that fit the bill.
So I need to stay Cdn tax resident, at least until I clean out the company - then I have no problem leaving.

 

[Sols]

Yes - if I understand it correctly, the Bulgarian-incorporated company would be dual resident but the tiebreaker rule in Article 4 of the treaty would rule that it is a Bulgarian tax resident. Maybe it would be prudent to build up some economic substance in Bulgaria to minimze the chance that they apply some anti-avoidance clause.

You might be able to get away with tax residence in Bulgaria through a combination of paragraphs 1 and 3 of Article 4, but there is also Article 5 regarding Permanent Establishment.

Basically, the company may be tax resident in Bulgaria but have a permanent establishment in Canada.

Then we have Article 7:

ARTICLE 7​

Business Profits

1. The business profits of a resident of a Contracting State shall be taxable only in that State unless the resident carries on business in the other Contracting State through a permanent establishment situated therein. If the resident carries on business as aforesaid, the business profits of the resident may be taxed in the other State but only so much of them as is attributable to that permanent establishment.

I.e., resident in Bulgaria but PE in Canada means income attributable to Canada are taxed there.

 

[WorldCitizen99]

Look up terms like: Permanent Establishment, CRC, Place of management, I'll add more if I can remember but these will help you get an idea of how this "corporate residency" stuff works. Not sure about any specific Canada tax treaties. Usually the "based on place of incorporation" is pretty meaningless if there is another country involved



I'm just thinking, if you can somehow decrease the value of the company legally e.g. by investing in a subsidiary in let's say Estonia, or loaning money to that subsidiary etc. I haven't really thought this stuff out too much but, you never know, there could be some loophole you could use to at least alleviate some of the tax burden.

Yes I've been reading about those terms. It's a lot to wrap your head around. I'd like to just be able to open a holding company with little economic substance and just let the tiebreaker rule force the issue but I'm willing to open an office and maybe run property management on a few airbnbs that I would buy just so I can get the treaty rate. I don't have much biz experience outside of helping my parents with their business when I was younger.

Hmmm....that 'loaning to a subsidiary' idea is intriguing - have to ask my accountant

 

[WorldCitizen99]

You might be able to get away with tax residence in Bulgaria through a combination of paragraphs 1 and 3 of Article 4, but there is also Article 5 regarding Permanent Establishment.

Basically, the company may be tax resident in Bulgaria but have a permanent establishment in Canada.

Then we have Article 7:



I.e., resident in Bulgaria but PE in Canada means income attributable to Canada are taxed there.

Since we're dealing with dividends, doesn't article 7 Business Profits only apply if Article 10.4 disqualifies the person from receiving the reduced dividend rate?

In 10.4, it says "beneficial owner of the dividends" (who would that be? - the Bulgarian company or me as a Cdn-resident-shareholder?)

In 10.4, "a contracting state" = Bulgaria
and "the other contracting state" = Canada since that is where the dividends are being paid from

but the first part of 10.4 says "beneficial owner of the dividends being a RESIDENT of a contracting state" - since I would not be a Bugarian resident, they can only be referring to the Bulgarian company, and since the Bulgarian company does not carry on biz in Canada, that whole paragraph should not apply to me, no?

It is rahter confusing

 

[KDX]

Yes I've been reading about those terms. It's a lot to wrap your head around. I'd like to just be able to open a holding company with little economic substance and just let the tiebreaker rule force the issue but I'm willing to open an office and maybe run property management on a few airbnbs that I would buy just so I can get the treaty rate. I don't have much biz experience outside of helping my parents with their business when I was younger.

Hmmm....that 'loaning to a subsidiary' idea is intriguing - have to ask my accountant

Yes it is quite a lot to wrap your head around. You then have to remember that nothing is black and white and you would have to have experience to know how this law is implemented and what you can really get away with.
It would indeed be a good idea to ask your accountant if you could use some tricks to lower the actual "fair-market value". It really depends on what they consider "value". You also have to be careful since this would be very aggressive tax planning and they could view it as tax evasion (again, you would need to ask a tax lawyer to know what you can get away with).

I wish you luck in this endeavor and please keep us posted on what happens

 

[Sols]

Since we're dealing with dividends, doesn't article 7 Business Profits only apply if Article 10.4 disqualifies the person from receiving the reduced dividend rate?

Maybe. Ultimately, the original point of these treaties is to reduce double taxation so you face the no more tax than the highest of the contracting parties, with allowances for exemptions for income which has little to no connection to a contracting state. Article 10 uses more vague language than article 7.

However, this brings up a point we haven't addressed yet.

In order for it to be dividends, the Bulgarian company has to acquire the Canadian company. How is that acquisition handled for tax purposes in Canada? Don't you as the shareholder face some sort of capital gains tax in Canada if you sell your shares?

It is rahter confusing

Indeed. Speaking with a good Canadian tax lawyer will give clarity on the matter.

 

[WorldCitizen99]

Maybe. Ultimately, the original point of these treaties is to reduce double taxation so you face the no more tax than the highest of the contracting parties, with allowances for exemptions for income which has little to no connection to a contracting state. Article 10 uses more vague language than article 7.

However, this brings up a point we haven't addressed yet.

In order for it to be dividends, the Bulgarian company has to acquire the Canadian company. How is that acquisition handled for tax purposes in Canada? Don't you as the shareholder face some sort of capital gains tax in Canada if you sell your shares?


Indeed. Speaking with a good Canadian tax lawyer will give clarity on the matter.

Ok the point you bring up about dividends is a good one. Yes, I had forgotten that a company can only pay dividends to a shareholder. And in order to become a shareholder of my Cdn company with its present assets, purchasing a share would be quite expensive. The only alternative I could see is to somehow create an empty holding company that is already partially owned by the foreign company, wait a year, and then find a way to transfer the assets tax-free but I'm sure the tax authorities already have a way to prevent a scheme like that. Yes and the sale of any shares would probably incur cap gains tax. Another good point. Like you said, a lawyer is essential.

I was reading about 2 landmark cases involving Canadian companies paying out (dividends in one and royalties in the other) to foreign holding companies and trying to get the reduced treaty benefit (Cases: Velcro and Prevost Car). The CRA lost BOTH cases. The issue was, can a holding company be considered a beneficial owner? And in both cases the tax courts ruled AGAINST the CRA and in favour of the taxpayer and so the HoldCos were able to receive at the reduced WHT rate. The court basically said that the HoldCos were not acting as conduits, agents or nominees and were not obliged to spend the received money in any particular way (therefore anyone who wants to mimc that result should structure their HoldCo with those conditions in mind).

So the options for me with their associated tax withdrawal rate would be:
47% - take it all out as a dividend then departure tax is not an issue (horribly high)
37% - get tax res in a treaty country, pay departure tax (26%) then use treaty to get the assets out at 15% (still too high)
27% - do surplus stripping which is basically selling a portion of the assets as a share and paying only a cap gains rate (accountant says this is a bit risky these days - maybe if I did over a few years?)
17% - set up a Retirement Compensation Arrangement (basically a trust with CRA where tax is only paid when money is taken out AND allows one to become non-resident and take out at 15% treaty rate) - but not sure if I can do this retroactively and do I really want to leave my money with CRA? The extra 2% is if I became resident in Cyprus and paid socials tax.
7-17% if I could make the above holding company scheme work

Or just continue to be tax-resident in Canada, live outside the country, take out just enough for living expenses and hope that the evil forces I see taking over my country will still respect the laws and not confiscate wealth or raise taxes too much. I could probably just pay 5-10% if I take out 75k/yr as a dividend. But I'd have to be careful not to stay anywhere long enough to fall under their tax regime, which sucks for QOL. Maybe Mexico is best compromise since they don't tend to enforce if u only have foreign income and don't transfer large sums of money into ur Mex bank acct.

My main concern for changing tax residency were:
-thinking there might be a windfall in tech/crypto in the future and I dont want to get stuck paying Cdn-level taxes
Solution: if I ever strike it rich, I could just declare non-residency that year?

-having to keep track of crypto and other investments when I wouldn't have to in a place like Cyprus
Solution: none

-being tied to what is see is excessive political risk in Canada. Obviously I'd still have to report any offshore holdings but at least keep most of the money out of immediate reach so it cannot be frozen the way they froze Cdn bank accounts for donating to a bunch of trucks that decided to drive to the capital.
Solution: keep all political posts anonymous

I realize this is a long rant. Any guidance or perspective would be appreciated.

Yes it is quite a lot to wrap your head around. You then have to remember that nothing is black and white and you would have to have experience to know how this law is implemented and what you can really get away with.
It would indeed be a good idea to ask your accountant if you could use some tricks to lower the actual "fair-market value". It really depends on what they consider "value". You also have to be careful since this would be very aggressive tax planning and they could view it as tax evasion (again, you would need to ask a tax lawyer to know what you can get away with).

I wish you luck in this endeavor and please keep us posted on what happens

Yes thanks for the well-wishes - I will let u know if there are any creative things I find out
Certainly, keeping assets in cash makes it pretty unambiguous as to the FMV of the company. One would have to keep it in the form of some asset in order to make the company look less valuable which would require a real artiste of an accountant and may or may not be worth it when you factor in the lost sleep worrying about how tax authorities will look at it.

I think the way to make the treaty thing work going forward is to gradually build up economic presence in the foreign country without triggering the departure tax and see whether I can direct some of the Cdn earnings to the foreign company. I was reading last night about the newer criteria that the CRA and judges are using to determine whether treaties are being 'abused' and there is a very comprehensive (leftist-biased) checklist of q's. It's way too ambitious for a lay-person like myself to take on. I think the good days of finding that rockstar loophole are pretty much over.

 

[Sols]

I was reading about 2 landmark cases involving Canadian companies paying out (dividends in one and royalties in the other) to foreign holding companies and trying to get the reduced treaty benefit (Cases: Velcro and Prevost Car). The CRA lost BOTH cases. The issue was, can a holding company be considered a beneficial owner? And in both cases the tax courts ruled AGAINST the CRA and in favour of the taxpayer and so the HoldCos were able to receive at the reduced WHT rate. The court basically said that the HoldCos were not acting as conduits, agents or nominees and were not obliged to spend the received money in any particular way (therefore anyone who wants to mimc that result should structure their HoldCo with those conditions in mind).

Not saying it's the case here, but a common mistake people make is comparing their small businesses to huge international firms and cherry-picking data. The outcome is one thing, but what are the details that lead to that outcome and is your situation comparable? Were there important arguments Velcro used that would or wouldn't apply in your case? Was the Dutch holding company a bona fide Dutch holding company, and not just an entity set up to evade taxation?

The case is 10 years old, too. Have there been developments since then?

My main concern for changing tax residency were:

-thinking there might be a windfall in tech/crypto in the future and I dont want to get stuck paying Cdn-level taxes
Solution: if I ever strike it rich, I could just declare non-residency that year?

Generally speaking, it'll be too late then. The event that made you rich has already taken place, and it will be taxable where you were resident at that time.

Any guidance or perspective would be appreciated.

Start off the new year with sitting down with a good tax adviser and plan for the future. You're good at doing research and can leverage that to make the most out of the adviser's time.

 

[WorldCitizen99]

Not saying it's the case here, but a common mistake people make is comparing their small businesses to huge international firms and cherry-picking data. The outcome is one thing, but what are the details that lead to that outcome and is your situation comparable? Were there important arguments Velcro used that would or wouldn't apply in your case? Was the Dutch holding company a bona fide Dutch holding company, and not just an entity set up to evade taxation?

The case is 10 years old, too. Have there been developments since then?


Generally speaking, it'll be too late then. The event that made you rich has already taken place, and it will be taxable where you were resident at that time.


Start off the new year with sitting down with a good tax adviser and plan for the future. You're good at doing research and can leverage that to make the most out of the adviser's time.

Yes these cases cannot necessarily be automatically generalized - you are right.
If I do depart, it'll come down to a calculation of how quickly I can recoup the big departure tax payment by living in a tax-free country e.g. Cyprus and investing the bulk of the nest egg in ways that are no/low tax but that will be for another thread.
Many thanks for your input and guidance!
Happy New Year!

 

[OffshoreMonero]

hehe
yes if I was a forward thinker, I would have scheduled an unforeseen boating mishap

This tends to be a common occurrence in the Monero community.

 

[aragon]

Problem
Changing tax-residency incurs a 'departure tax' of 26.7% of the fair-market value of the company (=cash value of company). So tax= $267K on 1M in cash assets. BUT that is just the cost of changing tax-residency.

I assume this exit tax is based on a "deemed disposal" of personal assets, and the (deemed) capital gain on them. The capital gain in your case being the gain in the value of your company since you acquired/founded it.

Some countries exempt certain assets (eg. local real estate) from their deemed disposal rules, and even pass that through in the case of them being company assets, under certain conditions, eg. said assets must comprise >80% of the company's value, and your share of the company must exceed 20%. If this is vaguely true in the case of Canada you might consider having your Canadian company acquire certain assets while you are still a Canadian resident. And a long time after you become non-resident, have the company dispose of said assets, and distribute the resulting funds as dividends or other disbursements.

You would have to discuss this with a local accountant who is well seasoned with these situations.