I don't have a lot of time right now to completely answer your questions regarding entertainment, etc. except to say there is a lively music scene, a comedy club, all of the entertainment at the School of Music, sports, etc.
For rentals I would recommend going to
HeraldTimesOnline.com - Bloomington, Indiana newspaper or
Rent Bloomington - Bloomington's Most Effective Way to Find Rentals. ( I am not connected with either of these sites. They are solely informational so I hope it's not construed as advertising. If they disappear, PM me and I'll resend.)