I hear people like the original poster saying they have been going to Gen Con for years and have always had a room downtown until this year and all I can think is "Wow! You have been so lucky for so long, I guess it was time for you to have a slight down turn"
Maybe that is harsh and I wish they could get a room downtown, but I do not feel sorry for them.
My buddy who has also been going for decades and really, really wants to stay downtown booked a room at $500 or so a night in case he did not hit the housing jackpot. That is what people who are prepared to pay for that luxury do. They prepare in advance and ready themselves for the cost.
I have been blessed to stay downtown and have had remote sites. If you cannot get a downtown hotel in the housing block or you do not want to pay exorbitant rates outside the housing block and you do not have a car, I highly recommend you rent a car for the duration and drive in and park. I have found this to be a much more inexpensive way of enjoying they convention from a remote hotel.
I went outside the housing block and got a two twin beds and sleeper sofa for $80 a night. We wake up and get cleaned up and then head into downtown where the $30 a day parking is just a few feet from the convention center. If we need to drop off purchases or gear, the car is right there. We go from 8:00 AM to 1:00 AM so there is very little need for us to go back to a room, although I understand that some might want to do so. In that case there is plenty of relaxing chairs and couches (especially in the JW Marriott) where one could take a rest or I could always relax in my car if needed.
I guess what I am saying is that we can complain about this and that and wish for this and that, but if we were realistic we would prepare a secondary hotel in advance of the housing portal opening and always have a back up plan when disappointment comes.
I did not want to sound harsh or unfeeling and I really do hope that everyone enjoys the convention.