If you're italian consider Malta as self sufficient.
You pay 0% on what you earn outside of Malta. Meaning that if you earn in another country
and receive the payment on a bank account
outside Malta you pay 0%.
Health Insurance is mandatory but with extremely reasonable prices (less than 500 eur x year).
I read (but warning: didn't verify) that is easy to do "tax" declarations. You don't need an accountant. Just someone who will teach you first how to do it.
It's easy to get residence,
if you meet specific requirements, but by reading your messages, it seems that you respect them.
Main cons:
- May be boring spending 6 months there. Maybe this can be reduced starting from the next year, as long as you don't spend enough time in places to become resident somewhere else.
- Need to keep always a real apt for rent, as far as I know. All year.
The correct solution varies from someone from outside Europe and an European. As far as I know, it can vary even if someone is from Italy vs someone from Austria.
I would think a lot about taking in consideration Dubai, as it has a lot of bloated prices, and some ethical problems. Maybe it makes sense if you have a $1M+ business. But as an Italian, I would check FIRST Malta. Not establishing a company there, but trying the self sufficient path.
As I had direct experience in this, I can tell you that these prices are slightly higher than reality. These are the prices that semi-scammers do for foreigners.
Some perspective:
Company setup: 150 to 300 eur. You also find professionals that will propose you the same thing for 2000 eur. You can avoid them.
Monthly costs accountant: 80 eur. If you have some connections with locals, 50 eur. Of course, I'm talking about a micro-company without a lot of invoices.
Residence assistance: you can do it alone, without the help of anyone. Just search on Google, and ask to the expats that you'll meet there. If you don't want to do this alone, don't go to an accountant for this. A lot of accountants charge up to 1000 eur. Consult a local lawyer that speaks english. Prices can vary from 50 to 250 eur. But honestly, it's easy to do it alone. You should do it with a consultant only if you don't want to "waste" those 1 or 2 half-days of queues. If your day rate is high, it may make sense.
Real apt prices are correct for a decent place, in the city center. In the capital can be 300 to 500 per month for something decent. 250 for something terrible and old, or particularly far from everything. With 700€ per month you start to get something really nice (almost at a "luxury" level).
In general, I found bulgarians to be way more welcoming and gentle than many other people around the EU. Living costs are low, and the quality of life isn't that bad, there are a lot of interesting (private) services and the main cities are modern enough. Internet connections are reliable and insanely fast.
The catch is that it's cold, too much, for too much time in the year. I hated that.