Chiang Mai? You clearly haven't been there!
It's nice for a holiday but not for living.
I can't think of a much better location for "Digital Nomad" (as much as I despise the term) than Chiang Mai, I would move back there in a heartbeat. Cheap amazing food, cheap and amazing accommodation, insanely friendly people, very strong and well connected expat / entrepreneur community.
Genuinely I am confused why in your experience Chiang Mai is a horrible choice. I think it is currently at the top of that list for a pretty good reason.
Chiang Mai is absolutely one of the most popular destinations for entrepreneurs in our community.
But maybe things are different when you really settle down.
Yes, it's a nice city for living but if you're not alone. Don't forget about the troubles about the visas and visa-runs.