First thing I do before arriving in a new place is making sure I have an accommodation for the first 3 days (AirBnB is always my first bet), that there are coworking spaces (www.coworker.com and the nomad forum are my best sources), and that the two locations are as close as possible.
In Chiang Mai, my best bet was Houzzel360, because it is nearby Punspace Tha Phae Gate … and this was an excellent choice, because both places are smack in the middle of the old town, where you can find most of the interesting things defining Chiang Mai. During the first 3 days, I was looking around for accommodations at a decent price, and soon found a private room just a few meters from there for THB 3000 p.m.; together with the coworking space (THB 3000 p.m.), I had a decent place to work and sleep for less than $200. I’m back in the same places after a year now, and I didn’t need to re-evaluate my choices.
It’s always a good idea to learn a few words in the local language, like sawat-dee-khrab (good morning/afternoon/evening), khob-khoon-khrab (thank you), khoa [beer chung] (I’d like [a chung beer]), … noy (…, please) and my-pen-rye (you’re welcome) for Thailand, because this is a real door-opener.
I usually dedicate my first 3 days in a new place to looking for an accommodation and place to work, roaming the city to get acquainted with the place I’m about to stay for a while, seeing where important shops like restaurants, cafés and 7/11 are.
Getting meals from the street market in various places (Night Market close to Punspace or street market at Chiang Mai gate), I have to add another THB 120 per day (THB 3600 p.m.) for food, which keeps my total living and working costs under $300 p.m. — not counting the drinks, massage and other stuff I afford beyond the basics at irregular times.
My standard of living is basic, of course, and not everybody’s cup of tea, but I like to keep life simple and focus on my work (not to mention the local girls, of course). At $300 p.m. fixed costs, it doesn’t hurt to add some luxury from time to time, though. =; )
Your mileage may vary.