YellowLab, I remember the Sheraton in Madison, right across the street. Stopped in to visit people there, but never stayed there. I think it was both pricey and always filled up fast. Since you could predict your assembly weekend from year to year, you could practically make your reservations as far out as they would let you. I seem to remember the Sheraton being very picky about non-guests being there. In particular, I remember one thing to do at night was to go visit your friends who had a pool at their hotel and go swimming. I think we did that once at the Sheraton, but they kicked us out for not having proof we were staying there.
I remember staying at various places on the east side of Madison near some mall. Quite frankly, I don't remember paying too much attention to the official hotel lists. At one point, I think we just started calling and found out who had the best rates. We'd toss out the JW thing to see if they had a deal (some hotels that weren't on the official list did offer deals) or we'd ask about corporate discount rates or AAA rates. I know quite a few times we didn't stay at official hotels because most of them were booked.
I remember my brother and I staying near the campus area once, knowing how cool Madison and State St. can be. But alas, things weren't very lively with college out-of-session.
cruzanheart, was that the tornado from a just few years ago? Like 3-5 years ago? That's fairly recent. Sort of assumed you may have been out of the org for longer than that.