#1. Get flight following. You don't even need to file a VFR flight plan and all the easy to forget about stuff that goes with it if you get flight following!!!

#2. Call the FBO's to confirm hours of operations and any good info. Use AirNav to help plan and check things out(this is my standard for trips to new destinations). I'd use this website to plan cheap fuel stops and alternates just incase you need them.

#3. Keep the cockpit clean. Bring all your charts you need etc... Just don't clutter the front end. Leave them reachable, but not in the way. Hard to enjoy a trip with stuff all over the place.

#4. Snack-Pack. Mainly, I just carry a water bottle, but on those days where I'll be stretching legs for max range, I'll bring some simple granola bars or something of that nature, and in that case a 2nd water.

Lastely, I've been to GWB(because it's just north of here) to pick up planes for Mx etc.. Good folks, should take care of you. Also, PCW is a nice airport. Never got services there, but there was always someone on Unicom to ask what you needed(even though we were doing taxi-backs). Since you're within 10nm of 3W2(Put-In-Bay) I'd recommend a due north departure over that island, it's just neat, then if you head on course from there you'll overfly Cedar Point amusement Park. Over KSKY you can get Cleveland App on 126.35 for Flight Following.(BTW, from Cleveland westbound to MKE I would say I have extensive knowledge of the area, so any specifics you need just let me know)