This isn't specific to you situation, but relevant.
First off, I have always lived with close friends, and its worked out great. I love having friends around that I can grab a meal with, watch a TV show or movie, or talk to about life in general. With strangers, you aren't guarenteed that.
My only negative roommate situation was when a friend moved out, and I found a random from craigslist.
Having said that, my current roommate situation, I found on craigslist, but after about 2 months, we were friends. Now after over 18 months, I'd say he's one of my closest friends. We are not the same age, he is 34, I am 30. But we are very similar. We are both neat. We keep all common areas immaculate. His room is a disaster and he never makes his bed, but my room is spick and span to the point that women call it "sterile." I don't like messes, I don't like shit left out, you'll never see dirty dishes anywhere, they belong in the dishwasher.
Also, I found that having ONE roommate is better than 2. With two, someone ends up doing far more work around the house than the other two combined, just how it seems to work out. Otherwise its a 2 on 1 and one dude ends up getting ganged up on. Never fun (ask rnch).
For your situation now, I'd lay down some ground rules about common area cleanliness, especially dishes, and basically let him do his own thing. He's got a different lifestyle, as long as he's not negatively impacting your's you should be ok.
Working from home out of the complex you live in is not something I would have suggested. Just too busy in general. Packed full of people who do not work during the day, noise levels could be high, thats more of a psuedo dorm that you live in.
Good luck though man. I wouldn't make any major decisions just yet though, get settled a bit.