they should totally do this for cooking schools. If your khao soi isn't up to Chiang Mai levels, they should deport you to New York or Italy with this pizza in your luggage:
Maybe ask if they can do any of the classes virtually. That way, you’d still be spending four hours a week learning, but you wouldn’t be spending time commuting back and forth to a classroom. So there’d be less of a hit to your productivity.
If you're starting out in Bangkok, almost anything you can imagine needing in terms of physical stuff is going to be available right in the supermarkets and pharmacies. Like, if you're tight on luggage space, don't bother bringing toothpaste or dental floss or shampoo, etc. The one big exception is supplements. Vitamins and other whatnot will often be dramatically less expensive and more easily available in the US. Think about stuff like melatonin or chamomile gummies if you use those for sleep, probiotics, and any other supplements you like to take as part of your daily routine.
Look up the cities where you'll be visiting on Google Maps and download the maps for offline viewing on your phone.
Actually, here's a map of places I like to eat in Chiang Mai, to get you started:
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Join some groups focused on things you're interested in (like, for me, it's foodie groups in Bangkok and Chiang Mai) and start saving stuff that sounds interesting in Google Maps. That way, when you're wandering around a city just enjoying the vibe, you can have sudden "Ooh! Awesome-sounding place x is right around the corner!"
Check to make sure you have an ATM card with a bank that refunds other banks' ATM charges and doesn't hit you with foreign transaction fees. (Schwab is really good for this.)
And a credit card with no foreign transaction fees is also helpful (Amazon and Apple both offer them.)
One other thing to bear in mind is that, even if you’re retiring to Chiang Mai, you might still want to take advantage of medical care like annual checkups in Bangkok — I’ve been really impressed with the checkup packages at both Bumrungrad and Samitivej Hospitals there. So, if you do find that there are a few weeks a year when Chiang Mai just doesn’t feel comfortable, that’s a good time to schedule your annual checkups in Bangkok.
Bear in mind that, in addition to burning season, summer gets quite hot, which might have health issues of its own if it means you’re staying sedentary by an air conditioner for a month. (If it wasn’t for needing to walk around the city exploring khao soi every day, I probably never would have left my room.) But it would probably be amazing to spend some seasons in Chiang Mai, and some in other parts of Thailand. (Or in Ubud, in Bali, if you’d rather be around temples and mountains instead of beaches, but still have a really good culinary scene.)