Open Source Cross Country Trip: Places to Stay, to See, and Tunes to Listen to

So, the route is pretty much planned out and so is the calendar, but that still leaves a lot of things that need to be done, like what we do at certain places, things to bring, etc.

We could use some help, so if anyone could help us out with the following, we'd really appreciate it.

1. Tunes - We'll need quite a lot of tunes on our trip, since we're spending three full days in the car, so if anyone would like to send over some mixed CDs, we'll check 'em out and give you a shoutout, plus a little review.  You can either e-mail me playlists or mail me CDs to 7423 Ridge Blvd., Apt. 1B, Brooklyn, NY 11209.
2. Western NY - We need to stop in Western NY on our way to Cleveland and we got a tip that Olean, NY has a decent place to say and that pretty close to St. Bonaventure and Allegheny State Park, so that looks like a go to me, but we've set out to spend a fair bit of time trekking through Western NY the next day and would like suggestions on places to stop along the 86/90 route west of Olean.  I'm thinking food, farms, nature stuff...  quaint little places that no one knows about, etc.  It seems like it would be a pretty quaint country drive if we found some nice places to check out.  Also, if there's a place in the Olean, NY area that you think is worth staying at, let us know.
3. St. Louis - What to do in St. Louis on a Wednesday morning?  Brunch?  Shopping area?  Something historic?
4. Sioux Falls, SD - Where to eat lunch?
5. Yellowstone - Best place to camp out and also where to go to buy a lightweight tent for two without breaking the bank, since its probably the only time we'll need one.  We're going to spend  a day in Yellowstone.