I haven't been to Gen Con in a decade - too much of a hassle when I've got Gamehole Con right here and can sleep in my own bed. But...
When last my family and I went in 2013 and 2014, we had 2 distinct experiences.
In 2013, we managed to get a hotel downtown and within walking distance. It wasn't directly on the walkways to the convention center, but it wasn't far off it. So it was nice to be potentially able to walk back to the room from the con independently - though we really didn't because the kids were 9 and 15 and we really didn't want them walking the streets of Indianapolis after dark. Then, since we were right next to a little memorial area that was the meeting place of some Harley enthusiasts, the night was really noisy. Plus, it was expensive. Another complication was we couldn't get all 4 nights (Wednesday - Saturday) - only Thurs-Sat. So Wednesday night, we had to stay on the outskirts of Indianapolis and drive in that first day (though, at least on the outskirts, parking at the hotel was free). So I suspect we were benefiting from a late-ish cancellation that freed up the space for us to snag.
The next year, 2014, we took the advice of some friends and stayed several miles away in a cheaper hotel and drove in daily. The hotel was cheaper (though a bit populated by truckers who were opinionated about the issues in Ferguson, MO that summer, which was... not ideal as far as we were concerned) and the drive was short at about 15-20 minutes. The parking, ironically, was cheaper driving in and parking in Lucas Oil stadium's lot since they were only charging $10/day rather than the hotels, with their own or shared parking structures, charging about $20/day. We had to coordinate our schedule even more, overall, but it was still an OK experience.
Getting events wasn't terrible, overall, for either year with most of us getting at least a few interesting things to do, though it is true that my elder daughter ended up playing a lot more pick-up games outside of official scheduled events. This was the heyday of Pathfinder 1e and we'd be packing the Sagamore Ballroom with the big events. I have no idea how it compares now, but events weren't hard to get overall, particularly if you wanted to play D&D or PF. That said, considering how Gen Con continues to swell at the seams, I can see how things are tougher now.