I am not in Max P, so I can’t answer all these questions. Will take a crack at the ones I know the answer to.
The ones I know of are here: https://housing.uchicago.edu/residence-halls/max-palevsky-residential-commons/max-palevsky-pictures/
The College has a standard bed frame and mattress combination that they use for most (all?) dorms. You can see it in the pictures above. These can be lowered or lofted (maximum height, IIRC, is maybe 1.25 or 1.5 yards), or bunked if both students want that. DIY lofting is discouraged, because done wrong it ends with a student’s bed crashing to the ground at 2 AM, and spinal injuries are no fun at all. There’s a process to request someone from Housing stop by your room and loft, lower, or even bunk a bed. This usually involves submitting a work order online - just as students would do for room or building repairs. See the “maintenance” section of this page for more info on work orders: https://housing.uchicago.edu/current-residents/services/
Yes to both, depending on how kids store other stuff. The smallest rooms I know of at the College have something in the vicinity of 80-90 square feet per occupant. Most are larger (the smallest single in my house is, IIRC, about 110 square feet).
Mostly, this will depend on how a room’s occupants store the rest of their stuff. If their laundry management strategy is a pile, and their notes cover two desks and 10 square feet of floor space, maybe not. But every room should have space for a few extra items, assuming some level of tidiness and/or creativity on the occupants’ part.
If you don’t damage the walls, Housing won’t care. I have a decent-sized poster collection and a towel hook I’ve put up on walls for two years now. Nails/screws are obviously a no-no, and regular tape might not be great. I recommend Command strips for easy removal at the end of the year.
Probably the right instinct. I would recommend a wait-and-see approach - buy the essentials, and give him some money to buy other stuff if it seems necessary after a week or two. Maybe reach out to the roommate over Facebook to coordinate on any shared items for their room. It’s easier than lugging nonessentials halfway across the country, and will give him a chance to see which items are actually needed and which are superfluous, shared by the house/dorm, provided by the College, etc. Plus, if he buys something and hasn’t used it two weeks later, it’s easier to return at a store in Chicago if it was bought there.