This is fucking inspirational! I'm about to take on a very similar journey. I'm also from NYC, 10 years older than you, but pass for 28 easily and act about 25, so I expect this trip to be highly entertaining.
My plan is to live out of a different city in SE Asia for 3 months every year (basically spend the shitty NYC winters there). I own a company that I hope to be able to run remotely for a few months out of the year. Bangkok is where i'm starting out, but I plan to spend at least a couple weeks exploring other locations to see where i'd prefer to stay next year. Also I feel you on the political comment lol.
My plan is to live out of a different city in SE Asia for 3 months every year (basically spend the shitty NYC winters there). I own a company that I hope to be able to run remotely for a few months out of the year. Bangkok is where i'm starting out, but I plan to spend at least a couple weeks exploring other locations to see where i'd prefer to stay next year. Also I feel you on the political comment lol.