My own experience at work totally backfired on me (interviewed as female, started taking T, then came out about two months after that and got fired), so I can't help you there. But as for housing, you can try living in a dorm/apartment complex thingy and it'll likely be okay. Yes, it's gender-segregated, but tell whoever's in charge of assigning people to rooms about your situation and they'll probably be understanding. I live in an extremely conservative place, and even here, they let me live in the men's apartments (I'm pre-op and can't bind anymore so it's totally obvious I'm trans).
Then, assuming that part works out, explain to your roommates that you're trans (or go stealth, if you think you can pass; even without T, you can train yourself to speak with a deeper voice. There are YouTube videos on how to do it). If the apartment manager/whoever is good at what they do, they'll probably put you with more open-minded people. Social proof is a powerful thing, so when guys in other apartments see that you live with other guys in the men's-only apartment, they'll be more likely to accept or at least tolerate you.
If all that's totally not what you want to do, casually mention that you're trans to someone who's subletting or whatever; the key is to not make it sound like a big deal (if you don't make it sound like a big deal, they'll automatically follow your lead and not think much of it, either; it's a weird social thing). Don't make it the first thing you say, though, if you can.
Also, when it comes to passing (if you decide to go stealth), confidence is actually more important than anything else. A few days ago, I was feeling confident as hell (not typical for me), and even though I can't bind and none of my clothes really disguise my chest, when I ordered pizza, the pizza guy got my gender right, amazingly. When you're feeling confident and if you learn how to lower your voice, it'll actually be easier to speak in a lower voice (that's how it was for me pre-T, anyway).
Good luck!
