Hi, I'm excited to bring my family to Gencon for the first time, but pretty disappointed in the clunky and inadequate housing portal system (I logged on right at my assigned time but nothing was availble. I only need a room Friday night. Any advice on how to find a reasonable hotel room given that everything seems to somehow be sold out already? I've seen a few "check back later, there'll be cancellations" messages, but is that really the only option? Tough to plan a family trip like this when I don't know if we'll actually have a place to stay or not.

Book a room outside of the housing block. There are plenty of hotel rooms available for everyone—just not always downtown or in block.

Check the websites of hotels by the Airport, they don't put all their stock into the Gen Con block so often still have rooms available if you go direct. 

You can also get a room at the Conrad. But it is $644 per night….

If you were trying to book downtown, note this restriction from the housing policy:

"Minimum night stay restrictions are in effect for all hotels in the downtown area. Requests for hotels in the downtown area must consist of three or more consecutive dates and must include the night of Saturday, August 3, 2024. Minimum night stay restrictions will remain in place throughout the housing registration period. Room assignments at suburban hotels are not generally subject to minimum night stay restrictions, though some exceptions may exist."

Plenty of other options, as noted by folks earlier.  Good luck!