We were lucky. In 2017 my son was only 2 months old for Gen Con, so he just slept in one of those baby wraps things on either his Mother or myself. All the background noise in the hall was actually nice as little babies like noise. So he slept most of the Con while we would game. This year we left him at home as he is a very active and grabby kid now and that would have been problematic, but not everyone has the option to leave their kids at home.
I agree with Marian, if you are coming with the a stroller, use the umbrella kind. But it is hard to get through the hall just walking, a stroller sounds like a nightmare to push.
Re: Kids... Leave the stroller in an out of way hallway (behind furniture or in the Training Grounds) and use a sling or baby backpack to navigate the Dealer's Hall and some of the larger con gaming rooms. My three kids have been doing GenCon since the fetus stage (they are now 21, 19 and 14); I would not have survived without my Mayawrap!
Regarding suitcases and the like... for the past 14 years, we've brought a smallish rolling carry-on with us to the Con hall from our hotel, to cart home our daily purchases as well as bring some games, DnD books for events, water and a few snacks. I first spotted this at GenCon where the two owners raved about it, and we've used it for many different conventions over the years. It is called a Zuca and you can sit on it, which makes it a godsend at the Con during gaming sessions, impromptu events in hallways and throughout the con when you need to sit and there just aren't many options out there. We do NOT take it into the Dealer's hall but leave it in some out of the way place during the day. I usually leave it with a friend who runs numerous gaming sessions in one of the adjunct spaces. I really trust the con goers and have never had a problem with anything being taken. Add a couple of bungie cords and you'd be amazed at what you can cart back to the hotel!
I can't see much below my chin without actively looking down and I wasn't expecting anything so low to the ground like that in a big crowd of tall adults packed so close together. Fortunately, I only shuffled into him a little (again, due to the crowd) and was then able to stop myself before really crashing into the stroller. It was scary, but his dad was super understanding. Little dude was somehow sound asleep, though.
Of course, you could make the argument that I was equally crazy for being there, I guess, but I had a guide 99% of the time.
As to OP's question, we drive up from KY and stay at an off-site hotel. However, we park nearby, so we take games back to our van throughout the day. The short walk is a nice break from the crowds. The van has pretty heavily tinted back windows and the lot where we parked was attended. No issues were had.
I wear a backpack and, if it can't fit in that, I'll usually make a trip back to the hotel every few hours anyway. As for getting it home, absolutely a duffel bag packed in your suitcase is your friend. One year, before I thought of that, I stopped at a Salvation Army store between downtown and the airport and bought like a $15 suitcase to get my stuff home.
Just to add my vote and nothing really new to the discussion, I use a backpack in the Con (I tend to not buy and walk around with large things like board games, I plan my purchase to be able to run to the hotel and drop it) and then check 2 bags (yay Southwest). On the way there it does make it a little awkward to have 2 lighter bags checked as they roll all over the place, but the extra space is very nice for the way back.
I wouldn't dream of trying to roll a suitcase through the vendor hall, though you could probably manage one through the ICC itself if you avoid the hall. Could split the difference and suitcase over to an entrance and leave it with someone, run in, buy whatever, and come back out I suppose.
Ill just throw in my two cents/play devils advocate on the stroller thing. I've been a solo dad since my son was 2 weeks old, and my daughter was 2 years old (they are 9 and 11 now). From personal experience, I can tell you that the person pushing the stroller is usually very self conscious about taking up room, etc but unless you want to always exclude yourself, sometimes the kids+stroller have to be there as well. Heck, I took mine to client meetings when my sitter fell through. Baby slings are life-savers but when they are little you also have to have the diaper bag, bottles, bottle of booze (ok, that one is for the parent but I digress), plus all of the things that go along with the baby.
As far as the stroller being knocked over most parents have ninja senses and are pretty good about avoiding that from happening and will do whatever they can to be conscious of the people around them. Just remember, that person pushing the stroller is getting less sleep than you, is under more stress, often covered in poop and vomit, and is generally the slave of a very small yet very demanding dictator. All they want is to experience the con and be a gamer for a while instead of just "the parent of the Grandparent's pride and joy".
I'm not saying all stroller weilding people are considerate, but many are. And if you see one trying to cross on of the exhibit hall intersections, you will make their day if you play crossing guard for them :)
Oh, for hauling the loot, I got a canvas messenger bag large enough to hold a 17inch laptop and it serves me very well.
And as for my kids, they stay with my parents during Gencon now days; this is Daddy's 4 day nerd out session and I think they are a little to scared to witness it :D
You can have a rolling suitcase in the Exhibit Hall if you're careful and conscientious about it. On Sunday, I planned to buy a bunch of stuff (both Zombicides, a few other large boxes), and there was no way my back could handle hauling all of that around the hall for several hours. I brought my small carry-on bag, and wheeled it around. Note that it is the kind that has 4 wheels, so it can be rolled standing up, instead of pulled at an angle. I had no problem rolling the bag directly in front of me, keeping it from inadvertently hitting people around me. Basically, if someone ran into the bag, they were running into me. I watched where I was going, and had no collisions, and no problems. It's all in how you do it.
I normally carry a light nylon sling bag that I can close, it use to be cloth shopping bags but changed over a few years ago. Everything gets dump back in my hotel when I get the chance.
I also do a lot of window shopping, for ordering of items on-line after Gen Con, that is IF the vendor sells on-line. You just ask them and pickup their cards or flyers, I will also take a note or picture of the item I am interested in.
Getting the stuff back home; well I drive up and have found the best way is to take a spare gym bag and just load everything into it.
Note: there is a package shipper (forget the name) outside the dealer room.
Anything that is small enough to fit into the backpack gets carried around until I get to back to the hotel at the end of the day. If the purchase is larger, then the shipping option is the best.
Since my daughter & I fly in...and we bring limited baggage...I limit my purchases to what fits in my backpack.
I have some in the carry-on, but again, space is limited. While I could pack a bigger suitcase and check it in on the flight, I actually like that my space is limited and I'm forced to better consider my purchases. The first couple times I've been to Gen Con, I was more impulsive with my purchases, but when I got home, not everything was as "shiny" as it was in the dealer hall. Some stuff I used, some I glanced over and put into the closet. Since then I've been more selective.
If I can purchase it on-line later when I get home, that's what I do (assuming I still want it). If it's a more custom/limited item that I can bring back on the plane, then I consider the purchase. Trust me, my luggage still comes home stuffed, ha!
A great tip that someone once posted was to bring an extra canvas (or whatever) bag that you keep rolled up in your backpack. If the pack gets too stuffed, use the extra bag for additional purchases. Since I've read that, I've always carried an extra bag like that. Plus, it's small so doesn't take up much space when not in use.
Another tip for the vendor hall if you have a backpack is to wear it on your front during the times you are in the hall. That way you can see the bulk you have on you and won't accidentally turn and bash people with your bag. If you can see it you are more likely to pay attention to it. If it is on your back you might forget how much space you take up.
I try to bunch my purchasing of larger items all at one time.
1- Vendor hall first opens to get anything that either I know will sell out, or that if it were to sell out and I didn't get one, I'd be very sad. Then the first chance I get to head back to my hotel/car I go.
2- Before the vendor hall closes. go back in the late afternoon and grab whatever you are going to get, drop it off before eating dinner/getting to your later events.
I bring a backpack and anything else I want throughout the day I buy and put in there. If its a big board game, I'll sometimes ask if they have plenty in stock and how safe I'd be coming back.
my best friend flies in every year and he usually brings a checked bag and puts his carryon sized bag in there. Packs it up and takes it back. Usually works. I think one year he had to ship stuff to me, so he used shipnaked.