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Best combination of high quality of life, entrepreneurial freedom and low taxes

English speaking country, your climate requirements and low taxes are very restrictive together :D

Mauritius has many ticks in your list...

but a 100% compliant country doesn't exists I'm afraid

Spanish language is super easy to learn and will give you few more options
Which Spanish-speaking options do you have in mind? The usual suspects (Panama, Costa Rica, Paraguay)?
 
An exact match to what you're looking for doesn't exist. You have to back down on some of your requirements. And maybe focus less on Wikipedia data points and spend some time in places before ruling them out.

Why are you looking at HDI? If you're rich enough, you can get all the amenities you're used to pretty much anywhere. What's considered rich enough depends on where you're going, and what you expect.

Malaysia, Philippines, Thailand, Costa Rica, Panama, and even Uruguay tick a lot of your boxes if you just approach them creatively.

As for big city where you can fit in as a European, you are missing out on some exciting places if you dismiss them because they don't have at least 1,000,000 inhabitants. A lot of countries don't have cities like that, yet still have plenty of activity from the local economy, expats, and tourism.
I totally agree on spending time in the countries, which is exactly what I am doing right now.

I am looking at HDI because when I was driving around for instance in the Bahamas it became clear that there is a massive separation between how the rich and the poor live.

You have these beautiful gated communities where everything is "nice" but as soon as you leave you feel like you're in a third-world country. I learned that this kind of lifestyle (being rich in a poor country) is not for me. I want to be able to just walk around and feel safe and comfortable. I want to be able to connect with locals and not just meet them because they are cleaning my pool.

From your list I'd say that as of right now I can't imagine Costa Rica, Panama and Uruguay because of Spanish. Thailand I spend some extended time in and was *very* happy when I left. Philippines is too crazy for me Over 7,000 people killed in six months in Philippines 'war on drugs', Malaysia is an option.
 
Taxes are of course not optimal in the US, but after spending some extended time in places where my tax rate would be 0% I decided that I rather pay around 20% and live somewhere nice than the other way round.
It will be around 30%+ in federal income tax ($500k+), but I'm not an expert.

You have these beautiful gated communities where everything is "nice" but as soon as you leave you feel like you're in a third-world country. I learned that this kind of lifestyle (being rich in a poor country) is not for me. I want to be able to just walk around and feel safe and comfortable. I want to be able to connect with locals and not just meet them because they are cleaning my pool.
Ough. Then you should first try living in Miami on a non-immigration visa. What you've described is relevant to Florida, albeit to lesser extend. It has a very different vibe from, let's say, Barcelona lifestyle.
 
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Interesting, I knew that Singapore is quite strict when it comes to politics but I haven't seen anyone calling it a dictatorship. Yet, looking at Capital punishment in Singapore - Wikipedia I think I tend to agree with you that it doesn't square well with my expectations of personal freedom :)

I actually forgot to mention that I also consider Malaysia, however I think all in all it is not developed enough for me outside of KL. The HDI is actually lower than the Bahams which I found to be quite underdeveloped outside of the hotel areas (List of countries by Human Development Index - Wikipedia).
Source: I worked with Singaporeans before in a job I once had and had many business trips there, all in all maybe a year in total spent on the ground
It is a soft dictatorship to be precise. Not something along the line from Stalin or Kim. But nevertheless it is heavily surveilled as well with millions of cameras etc. But they also leave you pretty much along.

It is nice but Id never ever live there, except for 8 figure salary or so. ;)
 
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Ough. Then you should first try living in Miami on a non-immigration visa. What you've described is relevant to Florida, albeit to lesser extend. It has a very different vibe from, let's say, Barcelona lifestyle.
Well, I spent a couple months in Miami / Bahamas / Dominican Republic and from what I've seen you cannot really compare these places in terms of feeling "comfortable" walking around.

I know that South Florida has bad areas but for instance in Miami I felt very safe going for a run through different neighborhoods in the evening while in the DR every supermarket had multiple security guys that were openly handling shotguns.

I've hung around quite a bit with locals in the DR as well and all of them told me that they actively avoid driving at night because it is that dangerous. Even local Uber drivers said that they wouldn't drive at night. I never felt uncomfortable driving around in Florida after dark.

Similarly in the Bahamas - I've talked to locals and all of them recommended to live in a gated community (if you can afford it) because violent break-ins are that common.

This is very different from my experience in the US.
 
Source: I worked with Singaporeans before in a job I once had and had many business trips there, all in all maybe a year in total spent on the ground
It is a soft dictatorship to be precise. Not something along the line from Stalin or Kim. But nevertheless it is heavily surveilled as well with millions of cameras etc. But they also leave you pretty much along.

It is nice but Id never ever live there, except for 8 figure salary or so. ;)
Great summary! I see it the same way - if I had a couple million I'd consider, but for now doesn't look like a great fit.
 
I appreciate the suggestions, however they don't fit at all to what I am looking for.

Monaco
- daily highs are below 20° for 6 months a year (Monaco - Wikipedia)
- no big city

Cyprus
- island
- no big cities
- not English speaking
- too cold, 4 months a year below 20° (Climate of Cyprus - Wikipedia

Italy / Greece
- not English
- high taxes
- not friendly for entrepreneurs
- also far too cold

Again, appreciate the help but these suggestions feel quite random and not really connected to what I describe as what I am looking for in the initial post.
I can't remember the last time we had 4 months of cold weather, so not a very reliable source. Temperatures are almost never below 20°, unless you live in the mountains. Even though English is not the first language, everyone in Cyprus speaks English as a very high percentile of the population are non-Cypriots.

As to your other points, agreed - there are no big cities, even though lifestyle, especially in Limassol is quite high-end.
 
Very interesting discussion! Let me add my 2 cents:

I know you “rejected” Greece already but let me make a case for Athens anyways: I (northern European) have spend a few months each year here for the last 10+ years:

PROS

+ Weather - One of the best in Europe.

+ English Language - I find that lot of people speak English in Athens and on popular islands

+ Athens is 1m+ size (so you find everything you need) and you can also drive to many surrounding countries. Or take the ferry overnight to southern Italy.
Or take a 1-2h ferry to amazing islands close by

+ Airport is well connected to Europe and Middle East

+ Mediterranean life, food, people

+ rents and property prices are still quite affordable compared to the rest of Europe (especially to similar countries like Portugal)

+ I feel very safe and find the development level sufficient. Sure streets and other things aren’t as new as in the north of Europe but you get used to it

CONS
- taxes high
- Government and government services often difficult to deal with (but with local lawyer it’s not too bad)
- government not considered entrepreneur-friendly , but I think they are trying to improve that

Overall I prefer Greece/Athens over all the other Mediterranean countries but that’s my personal opinion.
 
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I appreciate the suggestions, however they don't fit at all to what I am looking for.

Monaco
- daily highs are below 20° for 6 months a year (Monaco - Wikipedia)
- no big city

Cyprus
- island
- no big cities
- not English speaking
- too cold, 4 months a year below 20° (Climate of Cyprus - Wikipedia

Italy / Greece
- not English
- high taxes
- not friendly for entrepreneurs
- also far too cold

Again, appreciate the help but these suggestions feel quite random and not really connected to what I describe as what I am looking for in the initial post.
Monaco more or less what you need. You have whole France , Italy on your doorstep.
Monaco is pretty much English speaking. In winter yes, it would fall below 20. Mild winters and mild summers. You can spend winter in other place?
But I really don't know any country who would tick all boxes :)
 
How much money should someone be making to consider Monaco?
I would say you would need at least 1m cash to just thinking moving there.
You would have to rent (or buy apartment!) and put into bank 500k-2m funds , which would have to be invested and kept whole time of residence.
Thats the price of this serious residence

All other options are either not 0% income tax, or islamic or island countries
 
I can't remember the last time we had 4 months of cold weather, so not a very reliable source. Temperatures are almost never below 20°, unless you live in the mountains. Even though English is not the first language, everyone in Cyprus speaks English as a very high percentile of the population are non-Cypriots.

As to your other points, agreed - there are no big cities, even though lifestyle, especially in Limassol is quite high-end.
I agree with your point. Cyprus was actually quite high up on my list so I went there and spent some time in the different cities.

While it isn’t my favorite place in the world it wasn’t bad at all. I think if I wanted to stay in Europe and optimize for taxation I’d actually relocate there because it offers a great combination of low taxes and good lifestyle.

However I am not to keen on staying in the EU (which is a different topic), so it is not a great fit I think.
 
Very interesting discussion! Let me add my 2 cents:

I know you “rejected” Greece already but let me make a case for Athens anyways: I (northern European) have spend a few months each year here for the last 10+ years:

PROS

+ Weather - One of the best in Europe.

+ English Language - I find that lot of people speak English in Athens and on popular islands

+ Athens is 1m+ size (so you find everything you need) and you can also drive to many surrounding countries. Or take the ferry overnight to southern Italy.
Or take a 1-2h ferry to amazing islands close by

+ Airport is well connected to Europe and Middle East

+ Mediterranean life, food, people

+ rents and property prices are still quite affordable compared to the rest of Europe (especially to similar countries like Portugal)

+ I feel very safe and find the development level sufficient. Sure streets and other things aren’t as new as in the north of Europe but you get used to it

CONS
- taxes high
- Government and government services often difficult to deal with (but with local lawyer it’s not too bad)
- government not considered entrepreneur-friendly , but I think they are trying to improve that

Overall I prefer Greece/Athens over all the other Mediterranean countries but that’s my personal opinion.
Thanks for the reply!

I like Greece and thought about it as well, however I really dislike bureaucracy and dealing with lots of paperwork in a language that I don’t even understand is something that I am not really looking forward to.

I think Greece would therefore rather be a good candidate as “second country” where I would spend some time but not become tax resident.
 
I would say you would need at least 1m cash to just thinking moving there.
You would have to rent (or buy apartment!) and put into bank 500k-2m funds , which would have to be invested and kept whole time of residence.
Thats the price of this serious residence

All other options are either not 0% income tax, or islamic or island countries
Unfortunately Monaco is currently outside of my budget :( Given the other options I don’t think that there is a zero tax country right now that fits well. Which is not a big problem, as said earlier, I’d rather comprise on taxes than on lifestyle.