How does this work if you're not a citizen of that country? In this case your friend is an EU citizen, so that unlocks lots of options (like in this case work from Greece). I'm especially curious as Brexit is promising to ruin a lot of opportunities that would otherwise be available to my fellow Brits and I.
In the case of the American running a business from Crete, how does that work in terms of taxation and residency? People seem to get away with it in the far East, but (mostly) you can't just stay in a country indefinitely, mooch off the cheap system and pocket the difference.
I've studied the rules for Greece specifically. Currently for non-EU visitors, ~$24,000 in a bank account will get you a 'self-sufficiency' residence permit for 1 year. There are other permits available for buying property, marriage, and such, but thats probably not what a nomad would do.
That said, there it is not difficult to overstay the standard 90-day EU visa and simply pay the fine when leaving / on the next entry.
As far as taxes go, I would wager that any American in Greece is only paying taxes in the States. The Greek tax system is notoriously insane.
> That said, there it is not difficult to overstay the standard 90-day EU visa and simply pay the fine when leaving / on the next entry.
Don't do this. Customs officials really don't like it when you show a flagrant disregard for their laws. Also, you can create permanent problems for yourself if you ever decided to return.
I certainly did not imagine doing this on my own, nor have I tested the limits first-hand. The self-sufficiency permit isn't that difficult to obtain for a committed nomad, as I see it.
But the chatter in the Greek expat forums specifically describe the purely financial nature of the Schengen zone penalty: pay-to-play. The punishment comes in the form of the fine amount, which in a range is left to the discretion of the customs agent. Evidence of "flagrant disregard" or an otherwise spoiled attitude might get the maximum fine, whereas an honest mistake (or an engaging attitude) might cost only a few hundred euros.
If you don't have a visa, then you get 90 days in the Schengen Area every six months. You can head up through the Balkans (or elsewhere outside of Schengen) when your time is up. I used to go to Greece for three months at a time and then head elsewhere, like Argentina, Taiwan, etc.
I'm more interested in "short" long term options, e.g. a year or two. For pure tourism, tourist visas are more than enough.
Canada, for example has a Working Holiday visa which lets you remain for up to two years, travel and find employment (if you wish). There are restrictions: age, nationality and there are a limited number, but it's essentially a free ticket for 24 months.
Many (most?) countries have working holiday visas. The rules and availability depend on your own nationality and the country offering the visa, but generally they are for under 30's for up to a year. Some have a higher age limit, some are longer (as you point out), and some can be renewed for a second year if conditions are met.
If I'd known about this when I was young enough, I would have spent year in each of a dozen countries.
Make a name for yourself in some industry. The last time I looked for a job (around age 39), I sent out an email newsletter to about 9,000 subscribers and got back serious job offers in seven countries. I was sponsored by a company and immigrated to Austria on a work visa for technical workers. I would have gotten permanent European residence after five years, but returned to the SF Bay Area before that. There are ways to do it.
It looks like for the UK, you have the choice of CAN/AUS/NZ, Singapore, Hong Kong, Taiwan, Japan (pleasantly surprised to see that) and South Korea. There's also summer camp work in the US via BUNAC (which you pay for), but why bother when you can get a visa waiver for 90 days?
In the case of the American running a business from Crete, how does that work in terms of taxation and residency? People seem to get away with it in the far East, but (mostly) you can't just stay in a country indefinitely, mooch off the cheap system and pocket the difference.