I think I'm going to go with Regents. The facilities are awesome (the view from the Summit Club is breathtaking), the bus is extremely convenient (door to door service) and the prices aren't too bad if you split a 2BR. Plus, it sounds like its extremely convenient to have 50 or so other law students close enough you can visit in your PJs during finals week. I might move up north 2L or 3L, or to somewhere else in Hyde Park, but with a colorful as the neighborhood can be I think I'd rather wait until i've lived there to figure out the best places.
i'd put in a vote for university housing. i pay $800 for a really large furnished (full futon/double bed, huge desk with shelves, dresser, coffee table, two end tables, dinning table) studio with a bathroom, dressing room area, and full kitchen/dining area about a 15 min. walk from the law school, across the street from ratner, which is the big university gym. there is street parking, but i pay $35 for a reserved spot (that will run you over $100 a month at regents, where there is very little street parking at night). i'm one of the few who's sticking it out here my 2L and 3L year...it's just not worth the extra money to furnish a more expensive place up north for me.