If you’re a Portuguese citizen you can travel between 3 different countries each year and pay zero taxes. You need to stay 6 months in a territorial tax country to become a tax resident, so if you live in 3 countries for 4 months each, you’ll become tax exempt. Though you might have to pay social security taxes.

You sound overly sensitive. If it bothers you so much then don’t travel.

Personally I’m not interested in Colombia. Too many guys getting scoped or worse. Argentina, Uruguay, Chile, and Paraguay seem like much better options.

Good stuff. Yeah my team last year had multiple people in different time zones and everyone was expected to work on New York hours no matter where they were. We had people checking in from Cairo, Cape Town, and Copenhagen.

I agree it’s a good idea not to flex too hard on the people back home because jealousy is real. So only a few people would attend meetings from the beach or the swimming pool. Also if you ever screw up they might say, well so and so needs to come back to New York to prevent future problems.

Why don’t you take French classes? You might have a couple hours of classes per day, so you can still work, and you would get a student visa.

Bansko looks great. I would also check out the Bulgarian coast.

Do you have experience with Cape Town? Is safety an issue? How about Stellenbosch?

Both options sound very cold. I would consider either a warmer beach town or else a ski resort. Both Poland and Slovakia have nice ski resorts.

I think what he needs to do is hire a UK accountant to reclaim 100% of the taxes he paid to the UK government. Then hire an accountant in Estonia. You can probably set up an Estonia based company, wire your company a few thousand dollars every month, and pay Estonia taxes only on the amount you pay yourself. Estonia has a low tax rate so you might end up keeping more money even with accounting fees.

Yes. You get 90 days out of every 180 to visit other Schengen countries. Do you need a visa? Depends on what passport you’re holding.

Your first mistake is paying taxes in the UK when you don’t live there. UK is a territorial tax country. It sounds like you need to hire an accountant in both countries. Don’t try to figure this stuff out for yourself, you will just end up paying more. I have some expérience dealing with HMRC snd they are very difficult to deal with.

Yeah my understanding is that digital nomad visas let you stay in the country that issued it only. For the rest of Schengen you get 90 days. If anyone could travel with a temporary visa there would be no reason to seek citizenship.

As far as which one, I would avoid Portugal since it seems like Portugal is getting very crowded with expats. I have heard that Greece is one of the easiest ones to get.