It all depends on what you want out of and can put up with at Gen Con - how early you intend to be there in the morning, how late you expect to be there at night, how much stuff you intend to buy or need to lug around and how much of the crowds and noise you can take, how many late night games do you want to play, etc?

I can honestly say that the biggest difference between my connected stays and my outlying stays has been that it is easier on my spouse - I'm more of a night person and can stay out later with friends arguing over old gaming editions and she can head back to the hotel at 9 or 10PM and go to bed - or go back to rest and then meetup with me later.  Other than that, the experience isn't that different for us.  If we didn't have a downtown hotel, she'd drive back to the hotel, I'd Uber/Lyft independently and we'd probably come out ahead financially.  We're fortunate that we can afford to pay for the convenience when we have the option.

Don't give in to the FOMO!! Gen Con is great no matter where you lay your head at night.  Better to attend Gen Con and stay outside downtown than not attend Gen Con at all!

Back in the day in Milwaukee, I had friends who wanted the following from GenCon:
1) Game from 10ish in the morning to about 8ish in the evening.
2) Go do some serious drinking, interspersed with less formal gaming.
3) Carouse around downtown Milwaukee, including into their hotel, continuing to drink and game, and hang out with other drinkers and gamers.
4) Short stumble back to the room.
5) Repeat.

This entire plan changes if you have to include getting to and from a hotel 12 miles away (currently the closest available :) Waking and sleeping times change, available time to game changes, etc.

You're also right, however, that changing plans doesn't mean 'no fun'. People are amazingly adaptable, and they will usually enjoy things even when they change that they thought would be horrible. (Fact is that most changes in our lives that we think are big changes in the end do not affect our perceived happiness. Lottery winners are no happier than before, marriage or new jobs don't make us any happier...not getting a downtown hotel room is likely to be the same. You change your plans, you have fun. Even if you still fight for a downtown room next year.)

Now, of the 5 points above, 4 are related to drinking.  :).   If you don't get a downtown hotel, you can still do all of those things - except #4 - and then call an Uber/Lyft. Which is why I said "might better support it" and why you can *still* have that Gen Con experience while staying at an outlying hotel.

(I've liked my downtown stays, don't get me wrong - just want others to realize that Gen Con is great no matter where you stay)

Walking around all day and being able to walk back to your room for a nap, being able to chill out in your hotel lobby and store games in your room... Being able to walk back and forth to grab games, or go to a lounge (if you're in the Marriott) and get drinks, etc. is a HUGELY and wholly different experience than staying outside of the downtown area.

Knowing your car is parked and that's where it sits for the 4 days is a totally different experience too. You can get up when you want, go to sleep when you want, and you don't have to worry about getting anywhere or being anywhere other than walking down the the sidewalk or through a hamster tube. 

The feeling in the city is electric with gaming, too. It's like an entire city of gaming that doesn't sleep for 4 days and you never once have to remove yourself from it. No matter where you end up going if you're downtown, there are Genconners and people gaming around you, at almost all hours of the night. As you pass from the halls, to the gaming rooms, to the lobbies, everyone is constantly gaming, and you're enveloped in it 24/7. 

When you have to leave the area and get your car and go 15 miles out and go back to your room, it's a very, very different feeling. Doesn't change how fun the days of the cons are, but it's still a very different feeling. It makes each day feel distinct, as opposed to Wednesday night-Sunday being combined into pure GenCon.

It is great no matter where you stay - but the feeling, the experience, is much different IMO. Especially in the later hours at night when you have to go vs stay.

Indy needs to hurry up and build more downtown hotel space, and expand the convention center, or whatever they are planning. Add thousands of rooms, please. The more people who get downtown rooms the better, and GenCon will continue supporting Indianapolis. 

If just one person in the group wants to go back early? Second Uber, right? If someone wants to pop back to the room to grab something? Nope.

If you whitewash over the actual experience, then it looks very similar, yes. But if you look at the details, it's very different. Similar to comparing you and your friends hanging out at home vs going out to the bar. "You can still drink, have fun, etc". Yes, but it's a very different experience.

And that's just the example of those friends of mine. As others have raised, the ability to buy something large in the exhibit hall and bring it right back to your room. Or the ability of one of your group to pop back to the room for a nap. Or the ability of your entire group to wake up when they please, at different times, and roll over to the convention on their own schedule, without each one of you driving separately or taking a separate Uber, is a massive difference in experience.

Now as you rightly pointed out, that may not be part of everyone's experience. A couple attending together, wanting to get there the same time and leave the same time, not buying a lot in the Hall, not wanting the same kind of rambling night life as my friends--sure, outlying hotel won't be much of a change. But my own group is 7-10 people each year. We don't always do the same things, wake up at the same time--not even the ones sharing the same hotel rooms. An outlying hotel would be a significant change in experience. And I don't think we're that unusual. You're looking at it from the perspective of how you experience the Con--which is normal and fine--but there are a lot of people who do things differently, and a big hotel location change would be in fact a big change.

That said, I still agree that the majority of those people will adapt to the changes and enjoy themselves, even if they think they won't enjoy it beforehand.

IMO, the only scenarios where the experience would be totally different would be if you had limited mobility or small kids to look after.

So yeah, I'm not saying it's worse. I'm saying that many people will go into it thinking it will be worse the first time they have to change, but that for most people, it won't be really all that much worse at all. And in five years, they won't even remember it as being worse. :)

I'd like to throw our a clarification as well. I'm a single ex-farmboy who like to do everything at GenCon. Because of this, I can be up at 6 am, game from 8 until midnight and do over 60 hours of events throughout the weekend. Staying in an "outer hotel" saves me about $400 and gives me the twenty minute drive to cool down after a very long day of games. It's not for everyone but it's something to consider. I've done the downtown stay but the perks just weren't worth the extra money.
Side question: When you do stay downtown, where to you go for "necessities"? My hotel this year is walking distance to a Target but I wonder where people go downtown if they forgot to pack something like medicine or hygiene products. 

There are a couple of CVS Pharmacies downtown and the Circle Center Mall
 

There’s a Kroger downtown that does delivery if you need. Order enough and it is free. Many hotels have a “convenience store” for forgotten toiletries or some places just give you small samples. You could always Lyft or Uber to the store of your choice and back as well. 

When you stay downtown, you eat every meal at a restaurant (or food truck) full of gamers. The waiters might be in costume, they might have Star Wars playing in the background. When you walk between your hotel and the ICC you pass cosplayers and other gamers. Every surface in the hotel lobby is covered with games in progress.

When you stay further out, you can't leave in the morning until everyone in your group is ready. You might be downtown from 10am to 5pm. Then you drive out to eat dinner someplace quiet. If you drink it's with non-gamers. You retreat to your hotel room to play a game with just your group.

I will grant that if you're traveling alone you can spend the whole day downtown, spontaneously jump into a late-night game, and catch an Uber back to your hotel late at night. But if you're traveling with a group, you're limited to the smallest amount of "crowds and noise" that anyone in the group can take.

I have stayed downtown.  I have stayed 30 mins out.  I have had groups ranging from solo to four with myself carpooling.

Is downtown more enjoyable?  Absolutely there's a energy to staying downtown, it's more convenient and for me going solo cheaper because it's possible to find roommates downtown.

Does downtown make or break my con?  No, not at all.  I always find a way to work around my housing situation.  Hell half the time I don't even get a badge till housing lottery is well closed.

I certainly understand people have certain life circumstances which make downtown a necessity for there enjoyment.  I still think most people would be well served by embracing flexibility.

Fair enough. It wasn’t meant cavalierly. I’ve definitely been in a position where literally every penny counts and still tried to travel. My first Gencon, I was helping run a table and my room was covered or I couldn’t have gone. Before we drove out, I made food bags with meal replacement bars for every day. Dinner was PBJs in the room. Obviously if my ride was leaving, I had to go, too. Point being that there should be flexibility on both sides of the equation instead of one person controlling what everyone else does.

I think there is one point we are not really focusing on hard enough in this thread:

WOOOOO GEN CONNNNNNNNNNNN

I think the point here may be that an airport hotel that has free parking, plus Uber/Lyft is comparable cost-wise to downtown plus paid parking.  It might even be cheaper.

A downtown hotel is a deal-breaker for hardcore cosplay, people running games that involve serious amounts of material that needs to be transported, and differently abled folks.