Sure I get it. For the first stop, a beach close by is a big draw. Chiang Mai is fairly small with lots of useful stuff very close by and a great atmosphere. The Nimmamhaemin area is the main one cool area- bars cafés, co-working etc. + the Old city. In and around Chiang Mai there is a ton of natural beauty and things to do ( trekking/ hot springs/ mountain retreats etc) which make it great for having weekends away doing something fun. There’s loads going on here, but its not oppressive in any way.
Digital Nomad population is pretty high, so its good for networking and meeting similar types.
One for consideration for later I’d say. You’ll probably bump into people who’ve been here if you meet any nomads in Bali.
Congratulations on making your choice to head to SE Asia. I’m sure you’ll have a great time wherever you head.