Completely anecdotal, but seems like if you are going to book out of block, you start looking a few weeks after the current year - so beginning of September or so.  As time goes on, the rates go up.  Back in November, our room ended up being about $60 more than the Gen Con Housing rate.  We are fortunate that we can pay that premium and snagged one.

WAIT LIST
An automated Wait List feature will be activated within one week of housing registration opening. This feature will enable users to request additional nights on the front and/or back end of their assigned dates that are currently unavailable for assignment. Nights for which a room is currently unavailable but eligible for wait list will be denoted by a red exclamation point (!) indicator beside the date. Upon requesting dates that include one or more wait list nights, the system will monitor inventory and automatically add the requested nights as they become available. Upon adding a night, the system will also email a confirmation message to the primary guest email address.

Wait list nights included in your room assignment acknowledgement are not guaranteed until confirmed via new assignment acknowledgment.Dates required to meet Nightly Minimum Stay Restrictions cannot be requested via wait list. Attendees needing lodging during the convention peak nights Thu-Sat should check availability online periodically. As other guests modify and/or cancel their room assignments, online inventory will update in real time. Using the wait list function to modify your assignment carries no fee, and you can modify your stay dates at any time during the housing registration period if you no longer need dates that were assigned by the system after submission.

This is the second year in a row I’ve done this. I’ve NEVER gotten decent lottery time in many years of trying. 

So you could do what you are suggesting and still not get a DT room.

My group is good as we got lucky enough to secure rooms. I was just wondering if the out of block stuff had filled up as well or if maybe they held them until after the lottery since they have had issues in past years with people reserving out of block as a back up if they couldn't get in block (and if they did get in block then cancelled the out of block). 

The policy for the out of block the past two years was payment at reservation and no refunds after a day or two. In block still seems to be first day is paid in June and rest at convention. 

Yeesh.  Glad I booked an airport room.  Seems my time didn't have close to a chance at downtown.  

I just try to do the math on the normal room rate vs the upcharge in dollars. If it’s twice normal, but the points rate is reasonably normal, it’s an easy call to just book a rewards room.

I run my spending through my HH card. Try to save my points for Gencon trips, knowing that it’s the hardest to get dt rooms. But I agree that 70k for the Conrad isn’t worth it.

I had 1:58 and thought I was a shoe in for multiple choices, maybe not my first but there would be a few. When I logged in exactly on time only two left the Sheraton and Columbia Club. I got the Sheraton and am satisfied but wow those rooms went fast. Last year I had a late 2 o'clock time slot and got the Westin and saw at least half a dozen others.

I had a 5:40. Zero chance of anything close. Not going now. This is supposed to be a vacation. I am getting too old, not being able to go back to a room to drop stuff or take a break makes it more of a chore than I want.

to anyone that didn't get a downtown room, just wait till events go up. Once a few people don't get their events there are a few people who drop their rooms.

The best time we had (three people, three chances, no system gaming) was 2:52 pm.  Fortunately, I reserved a room downtown back in December as a "back-up ."  Looks like the back-up is the first-string option now.  It's more than the block prices - pretty sure it's more than the far in-block rooms + Uber/Lyft or car rental + parking pass.  But I'll pay more for convenience.