Seeking housing. Any tips?

[Loyal]

Recent events have led me to believe it's finally time for me to move out in the world. Granted, I still have a fair bit of schooling to get through, and I don't exactly have the networking to just pick up and start a new life somewhere, so I'm not gonna move halfway across the country or anything. Right now I'm just looking for a local roommate(s), something affordable and sufficiently close to where everything important in my life is.

However, I've never actually done this before, so I have no idea what I'm really doing. Right now I'm keeping my eyes on Craigslist and a particular subreddit, and already a few promising options have shown up. But I don't know if there are more options I could be using to search for housing, and I don't exactly know the "etiquitte" for handling these sorts of interactions in such a way that won't immediately get me rejected from consideration.

So, dear friends, acquaintances, and miscellaneous: any advice?