A series of posts have just gone live on my blog about "Getting to GenCon 2014". Would value any insight anyone has on what I'm saying in these posts.
Thanks in advance -
http://a2ndchapter.blogspot.co.uk/2013/09/getting-to-gencon-part-1.html
I think you're overestimating, by a little bit, how early and how late you'd need to arrive and leave if you want to experience all four days of the Con.
You don't need to arrive on Tuesday so that you can prepare on Wednesday, for example. I typically arrive on late Wednesday afternoon, check in to my hotel, and wander over to the Convention Center to pick up a program book, whatever swag is being given away (which gets to be less and less every year, to the point of being nothing at all last year), and stand in the Will Call line for any badges I elect for them to hold for me (which I typically don't do, as those lines are long that day).
Likewise, you don't necessarily need to leave Monday, either. The Dealer Hall is the heart of the Con, and when it closes at 4 PM on Sunday, it's like the sun is setting. A few events are still running, and maybe even a small seminar or two, but that's not very much; by the time 7 PM rolls around, it's pretty clearly over for all but the die-hards and those who haven't quite wrapped up their game.
In other words, try reserving a room for the nights of Wednesday, Thursday, Friday, and Saturday. Check out of your hotel Sunday morning; don't worry about your luggage, the hotel will securely hold it for you even after you've checked out. Fly in on an early Wednesday flight, and leave on a late Sunday flight; that should save you some time and money.