Do you have a dumb question that you're kind of embarrassed to ask in the main thread? Is there something you're just not sure about?
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Notes -
A) I am probably not a good guru as regards to this as I've only been to Chiang Mai once. Have you looked online? This seems to be in your window of expenses, but you need to think about things like health insurance, to say nothing of daily/weekly laundry costs (there will be places that can do this for you relatively cheaply, and fold up your shirts, etc.) I presume you'll need a good internet connection? There are subreddits about Chiang Mai that might prove helpful. This is the kind of thing where Reddit is actually useful, to some degree, though don't expect consensus opinions.
B) I cannot imagine, as you say, eating out for every meal. That seems pointlessly tedious, in addition to probably not cost effective. A rice cooker will take you a long way, as well as a small fridge and a basic knowledge of cooking that you'll need to develop anyway as a functional human being.
Public holidays or days when whatever cafe you frequent are closed will happen. In terms of street food that locals eat (that you buy on-the-fly and either eat sitting on a bench or wherever) the food basically sits out. It might have ice near it. I noticed oddly in Bangkok that the street food stalls smelled really strongly (of spice, etc.) but had no flies anywhere, even in the 80F weather in February. I thought that was weird and I still don't know why there weren't more flies. I did not eat the street food. Some of it looked good, but I didn't want to chance it. A friend of mine got what was probably food poisoning once eating Chiang Mai sausage (though he was in Phuket.) It may not have been the sausage (I like Chiang Mai sausage, actually, though it is spicy.)
C) You make it sound like you will hole up in one apartment semi-permanently, only venturing out to eat with your roomie. That sounds like hell to me, unless you are very close to your roomie, and even then, yeah, Hell. But I'm not you.
I can't offer you much else, other than what I've already said regarding transportation--and I expect even if you don't "commute" to and from any work, at some point you'll want to get out of the neighborhood and explore, particularly if you're staying there longer than a month or two.
Many herbs and spices such as lemongrass, cloves, and chili peppers have natural insect repellent and antimicrobial properties, which helps explain their prevalence in tropical cuisines and perhaps the lack of flies.
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