I'm always amused at FTers who occasionally look to drop hotel points on 5* for a place like Chiang Mai or even Bangkok (not directed at anyone in this thread, just generally). There's so much competition that the sweet spot on prices can be low. For CM I usually aim for something like the Suriwongse or the Pornping at $30-ish or so. Both were once near the top of the market but are now cheapies in the middle. The Suriwongse is the better of the two and very close to the night bazaar. I've never felt unsafe in that part of CM, but some areas aren't the most pedestrian friendly and with all the motorcycles zooming by there might be some problem with snatch-and-grab bag thieves, though still nothing like Vietnam.

CM in general I just haven't been able to "get" why many like it so much. Prices are very low and it works as a base for nearby attractions like Wat Doi Suthep and the treks, but the city itself seems like a battleground between motorbikes and pedestrians. Khorat (Nakhon Ratchasima) also has a moat and the same kind of dynamic but gets far fewer visitors.