Time is going to be the problem here. My 2 cents: meet in Chicago area (or whatever the best central location is?) Monday AM and shoot straight for Monterey. Arrive Thursday AM. Run down to LA area Sunday evening with the local boyz, prep the cars for shipping/storage and fly out Monday night.

Logistical problems: where do we stage the cars for shipping back to the midwest? Where do we ship the cars to? How many cars are going? We need to keep this to a manageable group. i.e. The more cars we have, the more stops, the more potential breakdowns, etc. We need to figure out how many cars we can get on a transporter - six? Sounds like we've got at least 2 cars that will stay in LA.