Myself, my husband, and friends of ours went last year and were only able to secure a hotel room thanks to the kindness of someone on the Friends of GenCon page having a last-minute cancellation. I honestly don't know enough about the area to know what hotels are considered the "closest" to the convention center or not - but I am scared that I won't be able to get a single room (all we need) for this year based on the fiasco that was last year's hotel "holders." I know the newer policy aims to get rid of folks holding, but I'm nervous it won't shake out that way. We're coming from over 5+ hours away by car and am the logistics person/organizer so I'm actually genuinely nervous about not getting a hotel room.

For those who were able to see/get a hotel after the initial grab/it went back up on the market, how often did you check/did they go up? Is it consistent at all? Or does anyone think there will be a shift/more vacancies because of the policy change?

I feel your anxiety.  In the past, I've checked housing obsessively to get a room.  Like a few times a day, every day.  It is time consuming, but I've eventually gotten a room each time.  It's a pain.  I think it is more likely to get a room closer to the Con then right after housing closes.

I work at a computer desk, so my hope is that I'm able to sit and watch during the work day if I'm not able to secure one right away/on the 11th. If you've been able to secure one each year by doing that, it does make me feel a little less stressed. Thank you!!

Are there hotels that are "closer" than others, in the (unlikely) event I do get a choice?

The rest is cost and availability

This list of hotels includes their distance to the ICC.
https://www.gencon.com/attend/hotelmap#downtowncampus
And here's a map:
http://cdn.visitindy.com/map/VisitIndy_Downtown_1117.pdf

Even if you don't get a good draw in the lottery, there are plenty of hotels within a 30 minute drive. Your choices are not limited to the official housing block.

I always say that people get way too stressed out about getting those downtown rooms.  If you can't get one, then you can go to plan B.  Get something at an outlying hotel and drive in.  You can park at the World Wonders Garage in the Circle Center Mall for $22 a day.  That is right next to the convention center.  If you are driving in, you already have your car, but if you are flying in, you can rent one.  The cost of parking + car rental + hotel room outside of downtown will be cheaper than a downtown room.

Look at it this way.  I live in Indianapolis, about 6 miles away from the convention center.  There are 3 motels within a block of my home: a Super 8, a Travelodge, and some local brand I can't remember.  I didn't bother to try and get a hotel room downtown just to be moderately closer.

I realize it may be a bit more expensive to stay downtown, but when it's already a long drive to get there and back, I don't feel like it's ludicrous to hope for a hotel where we don't have to drive any more.

Thank you @selene314 for the lists with the distances. :)

Downtown rooms are readily available if money is no object, but not everyone will get one via the hotel lottery.

And, if you don't get a downtown room (and are unwilling to pay exorbitantly for one), there are plenty of non-downtown rooms available. And you still don't have to drive: just take an Uber of Lyft.

_____________________________________
Alec Usticke, Fans of Gen Con Facebook Group

They do not seem interested in a working shuttle program. So you will have to drive or taxi it unfortunately if you don't win the lotto.

I drive from 14+ hours (DFW) and I like to stay downtown, but usually I have to get a remote site. As my lottery times were so late (after 6:50 PM) this year, I will probably not be staying downtown. I have been remote the last two years and it is really not bad.

I pay for parking, about $30 a day at one of the sites right next to the convention center. If I need to drop stuff off in the car, I can. If i need to rest, I can.

There is no need for a downtown room for ANYONE in my opinion, it just nice to have. There are always work arounds, but people just need to be open and flexible to them. Even if you have a disability, the close by hotels are still a hike, some much farther than the parking garages. Even if you need to rest, there are ways to do that in chairs and rooms that I have found readily available around the convention center.

If you have to drive back and forth in turns to a remote hotel, that is also doable. Again, downtown is nice, but really should not be a do or die for anyone in my opinion.

I am sure I will take flak for this controversial opinion from those who say I do not understand their situation, but where there is a will, there is a way...

note for those with bad time spots. when events go up they put parking tickets up with a regular shuttle to them. I did it last year and it was ACE. Last year the parking with shuttles i think was 50 dollars for 5days. I found i could drive from the airport in around 15 minutes and the shuttles from the parking took 15 minutes to get in, or you could walk to the stadium in 10 minutes.  I'm from the UK so hired a car at the airport for the weekend.

overall? its cheaper than the downtown hotels even if you include the car hire, the rooms to the south of indiapolis, or near the airport can be quieter than downtown, and most are full of gencon attendees in the morning anway. I gave lifts to fellow con goers and other did the same.