Well, you will want a table saw, a sliding arm miter saw, drill drivers, lots of screws, drill bits, a circular saw,
jig saw,
router, angle grinder, belt sander, other sanders, other
hand tools, measuring tape, pencils. Stuff you might want: MIG welder, plasma cutter, band saw, scroll saw, drill press, dust collection
system, steel saw, a painting area, a flammable
goods cabinet. At any rate, in your situation, you will want a lot of brooms. How
portable all this is is really a decision you need to make at the get go, because something like a saw stop (i dont see any reason for a school to buy anything else) generally needs dust collection and a solid
base. Drill presses, bench grinders, belt sanders,
etc. require solid mountings too. My guess is that if you can help it, you will want a nicer shop and tools, that way you can
build more complex sets, and be building while you
load in. Also, you will want some place to keep a flammables cabinet for the numerous stuff that can
burn in the shop. A paint area is usually nice to have, but can just be as small as a corner with a sink and some shelves for paint and a rack for brushes (thats all ours is). I think the biggest issue might be where to keep all this stuff. We have a sizable room just to store all of our tools, and a lot of them dont really fit in there that well (all bench mounted and free-standing tools are not moved, for obvious reasons).
However, I work at a college, we have a fairly large scene shop, and have put thousands of dollars a year for the past 10 years into the shop tools and whatnot. Your situation might warrant different tools, probably could save on the metal working tools and stick to wood. However, I think its probably a decent idea. I really like the idea of a Conex that you can fold out or something to make an outdoor shop, but in Chicago, you wont want that.