I don't know if DBQ has any place to pitch a tent. Those are both my typical stops (decent cafes at both of them), and I usually spend a little time at DBQ, have lunch, and then head off for OSH. Per the NOTAM, you either have to get in there pretty early or wait until the airshow is over, so I try to time it so that I arrive at Fiske just as the airshow is finishing. I've had 2 years where I waited around at DBQ too long and barely made it into OSH before the airport was closed--one year I was the very last airplane in.
Flying in really isn't all that hard--the
anticipation of flying in is a whole lot worse than the actual flying. If you
know the NOTAM, and follow its rules, it's really pretty easy (you don't want to be reading the NOTAM for the first time just as you're coming up on Ripon

). Last weekend I did some spot landing practice, which is a good idea, as is knowing your power setting to maintain 90 knots airspeed from Ripon to Fiske. Make sure you can stay on altitude consistently, and keep your eyes open for other airplanes (obvious, but sometimes I haven't been sure that others are doing that!).
Mostly have fun. OSH is a blast!
Cary