Adam, just fly into OSH. The drive from Appleton will quickly become your biggest PIA -- it's NOT an insignificant commute -- and you will regret it forever.
To your point, however, there are many things you can and should do to maximize your enjoyment at OSH:
1. Wear different shoes every other day. I alternate between two different pairs of Ecco sandals and comfy tennis shoes. This will prevent/minimize blisters, as you WILL walk 5 - 10 miles per day.
2. Wear a LIGHT COLORED hat, preferably with a big brim. I'm always amazed at the number of pilots I see at OSH wearing black baseball caps, baking their brains (and their ears) in the July sun.
3. If it's really hot (and the hottest I have EVER been is in OSH, and I live on an island in the Gulf of Mexico!) you cannot consume too much water. Getting your loose-fitting cotton shirt wet helps a lot, too.
Oh, and bathe in the spray-on sunscreen. It works.
4. If it's cold (and that has only happened once, in 30 years) pack a sweatshirt and wind-breaker. That's all you'll need.
5. The airshows are fun for a day or two, but the REAL fun is out in the North 40, watching arrivals/departures after the daily airshow. If they're using Rwy 27 (the norm), the departures will be right over your head, so we usually set up our chairs out THERE, rather than on the Rwy 18/36 flight line.
Some of the landings are more, um, aerobatic than others.
6. If you really want to see the big exhibit halls (with all the aviation goodies for sale), plan on hitting them DURING the airshow, when the crowds diminish. It also helps to hit them early in the week, before all the exhibitors get the "1000-yard-stare"... (BTW: I have not noticed any "fire sale prices" near the end of the show in the last 15 years, so don't worry about "getting a better deal later in the week". Ever since Garmin came to dominate avionics, they set the "firm price" tone that now rules everything at OSH, and the days of scoring a great deal on the last day of the show seem to be over.)
7. Do NOT miss taking the bus over to the Seaplane Base. It's a little piece of quiet, cool, heaven in the middle of the action-packed, blazing hot AirVenture. If you can swing it, go there on Friday night for their traditional Wisconsin fish fry. It rocks.
8. Food suggestions. Be sure to eat at Friar Tuck's, just through the North fence of the North 40. It's been our "first night in OSH tradition" for many years, and our group just keeps growing.
Other great restaurants in that area (all walkable from the North 40 -- driveable, for you) are the Charcoal Pit (great lake perch), and LeSeur's (for a great breakfast).
The Hilton also has an all-you-can-eat breakfast buffet that's pretty tasty -- and you get the added fun of eating breakfast with Harrison Ford, Chuck Yeager, Bob Hoover, and whomever else of the Big Wheels of Aviation might be in attendance this year.
The on-field Zaug's food is...okay. We mostly try to avoid it, although some of their stuff isn't half bad. It can be VERY spendy, though -- so for that kind of money I'd rather eat at Friar Tuck's and have some pretty young thing waiting on me...
(An aside: NOTHING smells like Friar Tuck's in the evening during OSH. Take 400 guys who have been sweating profusely for 12 hours, roll them in dirt, and then get them to all sit down in a nice restaurant. Luckily, we all smell the same -- but I don't know how the waitresses can stand it.)
My advice: Make this an annual event. Don't try to see everything, because you will not be able to do it. This will be our 30th in a row, and I could literally spend the entire show in the Warbirds section. Instead, we spend a day there, a day in Vintage, a day doing the buildings, a day...
We leave in 29 days. I can't wait!