Choosing to start in Chiang Mai, Thailand was fortuitous. It really is very convenient for digital nomads. Monthly renting is easy in Chiang Mai. Lots of great food and co-work spaces options. Good internet all over. It is an easy and enjoyable place to live.
I started my digital nomad ways a bit differently than most (though largely in similar ways). I lived in Malaysia a couple years first and then set off to be a nomad. I just sent two boxes a bit bigger than those for a ream of paper back home before I left. And I gave a bunch of stuff away I had picked up (books, printer, basketball, plants, cloths, etc.)