This is the first year out of the last ten that I was not able to book a downtown room connected to the convention center on housing registration day. This is also the first time in ten years I will be dragging a 7 months pregnant wife with me. After diligently refreshing the housing portal these last few months, I managed to land a connected Marriott room.
To anybody in a similar situation, give yourself options. I booked a refundable room out of block around the time of housing registration. I constantly checked both the housing portal and third party sites for the best deals. Most importantly, be aware of the important dates that people will be thinking about gencon. Dates like event registration, the day cancellation fees for block hotels go up, and deadlines for event submissions are all times where there might be churn in the housing stock. Good luck for everyone still looking, there is still hope.