It sounds nice if you can pull it off, but on the occasions where I've been continually moving from place to place I've found it much harder to actually get anything done. Continual travel adds cognitive and other entropic overheads which deplete your mental and energy real estate.
Yes, i have the same problem. Many times i thought, that i will build something while traveling, but that never happened :) Though as far as i understood, they solved this with going out as tourists only on weekends.
Again GTD is a good way to make your way through work.
Also: when you're on the road, you won't need to go and see family and friends. You'll miss them. But a lot of time is free to do other stuff.