If I'm not picky, and just want some room connected to (or within walking distance of) the convention no matter what lottery generated time I get, is that likely? Or probably too much to ask?
Is there a page that describes how the lottery works?
Although I'm not familiar with the lottery system, I don't think it's complicated and Rong explained it all. It's a lottery system which means that you are randomly assigned a time when you can access the housing portal. If you are lucky, you get an early time and can get a good room at a good price. If you are not lucky, you get a later time and you can't get in until all the good rooms have sold out.
From what I hear, all the rooms within walking distance sell out. An outlier hotel is not terrible, although of course anything you buy at the convention you will have to lug around with you all day. I am sleeping in my apartment of course, in southern Indianapolis right off I-465 exit 2. Each day of the convention I drive only about 6 miles to get to my parking space. Now my parking space is a mile from the convention center, but the only reason I don't park closer is because I work downtown and I'm already paying a monthly fee for that space. However, near my home there are 4 hotels: a Holiday Inn, a Super 8, a Travelodge, and some seedy looking no-name motel. You could probably Uber back and forth. I don't know what that would cost though. You can also take the Indygo number 22 bus in to town on Thursday and Friday (number 22 doesn't run on weekends). It stops at the transit center a few blocks from the convention. I wouldn't try to take the bus to get back though.