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Digital Nomad Perpetual Traveler + Apartment in Cyprus = tax ?

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That's why I suggested him to contact the tax office and ask what kind of information they want to see.
Just don't use your own name and don't call the one responsible for your. They may get suspicious and check. But there are many people here that left Germany and I can tell you that it is a case-by-case game.

You have two options. Either go down on profits and deregister then fly under the radar (can be coupled with a residency in Bulgaria/Switzerland etc. and train travel to Germany while paying some tax there. Alternatively, you move to a country with a DTA Germany, read the rules and fulfil those. This will be hard as you still have the PE risk in Germany unless you have substance (a girlfriend being director in a office) elsewhere.
 
The PE risk really seems negligible to me if there are no German clients, he really doesn't have an apartment in Germany etc.
If he leaves Germany with a last profit of 20k EUR, the risk of them chasing him is also negligible. Just don't go to Cyprus, Monaco etc. where people normally go when they do have money. Take Bulgaria or the Philippines and keep traveling. If you need to stay in Schengen area Bulgaria would be best if you then travel to Germany by train.
 
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