I think it will be very hard to manage, since you will need documents every time you change countries and its a huge hassle on your part. But if you're willing and you can, its a good choice to avoid taxes.
It's a lot easier than what most of you think. I work online so moving isn't an issue. My companies are registered in stable countries, they do not move with me. They bank in Singapore, UK and EU. I do my personal banking in Hong Kong. I'm domiciled in a tax haven and my country of citizenship has accepted my expatriation (Canada). I stay on tourist visas, they usually allow me to remain in each country 3-6 months.
It was a bit of work to setup everything but I've been doing this for nearly five years so it's been more than worth it.
I still visit my family every few months as I used to do before. As for friends, I've mostly made new friends who also live like me and we meet in different countries. I tend to spend a lot of time in the same cities so I also have local friends there.
It's a lot of fun, if you do not have kids I recommend giving it a try. As an added bonus, you'll be able to wipe the word taxation off your vocabulary.
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