My daughter & I both enjoyed 'The Naked Roommate'
http://www.amazon.com/The-Naked-Roommate-Issues-College/dp/140225346X. It's humorous at times and quite frank about some issues such as drugs, alcohol use and sex. It's a sensational title but it's really a down to earth book that gives good advice of how to get along with roommates. One of the big take-homes DD got from the books is you will be a lot happier if you don't EXPECT that your roommate will be your best friend. The month before my daughter went off to college we spent time reading various chapters out loud and discussing them.
Edited to add fiction rec:
Fangirl a Novel byt Rainbow Rowell.
http://www.amazon.com/Fangirl-A-Novel-Rainbow-Rowell/dp/1250030951A story about young woman entering college and her conflicts with her twin, her roommates and her online fandom life and how that affects her studies. I recommend it what I like is it's very modern and shows current stresses and anxieties about being a college student. I honestly don't read much in this genre so I don't know how it really compares.
