Subj? And 'living' means not just travel but paying staying considerable amount of time and pay income taxes in these countries. Please note, due to US tax system any American is required to pay income tax in US even when he/she lives abroad.

I am not talking about these cases - I mean cases when several month per year are spent in countries A/B/C...

Question is - what is most difficult (apart financial) with this lifestyle? What are hidden pitfalls?