I tailgated at GG for 3 games last year and honestly everything went pretty smooth.
I showed up at 5 PM on friday and I pretty much the entire place to choose my spot - there were only a few frats and RSO's also setting up.
I expect it to be more popular this year though.
I pretty much just set my stuff (awning, grill, chairs, bags, cooler with un-iced beer) in a pile then went home. The next morning i would park in my lot (46 at the time, 42 this year) and walk over with my stereo, bag of ice, and food. I bought a camping wagon this year to make this process easier.
I've never had an issue with anything going missing over friday night or during the game. After the game we may go back out and slam a beer or two. someone would then bring the truck around to the lot just North of GG where we unloaded and we'd load everything back up.
It all goes pretty smoothly really and you can't beat how close you are to the action. The drumline and band come and give a nice concert as well. And the illiniwalk was more popular last year than I've ever seen it before.
I highly recommend it and I'll see you there on Saturday.