I don't think I've ever gotten the requested room, or anything close to it. Most of the time, it's worked out well. Last November, not so much. Solo female traveler, and I ended up with a ground level, handicapped accessible room. I HATE ground level (my brother's ground level room was broken into via the window one night while they were in the room, sleeping) and also don't do well with HA rooms. I have terrible knees, and both the bed and the toilet were too low; it was really hard to sit/stand. I was so unhappy with my small, dark, first floor room. It really did take the "shine" off the trip a little bit.
I just put in a request for my Nov 4-8 trip to ASMusic via touringplans. I asked for a room range, but in the notes specifically requested upper floor, NOT handicapped accessible. Those two are far more important to me than the actual building/view.