An ultimate tailgate with an unlimited budget? I'd get one of those smokers built on to a trailer and show up the day before to start smoking some pork, throw in some ribs and chicken the next morning. Brats are very good and fun to eat at a tailgate, but child's play for an ultimate tailgate.
In Ohio, cornhole is a must at every tailgate. The game (
http://en.wikipedia.org/wiki/Cornhole_(game)), not the kind of stuff that goes on in the pirate ship.