On planning a plan for a plan to plan

I'm testing the water here, but I'd like some input from you guys. My father will tell me I'm mad. BLS already has done. Here's my (loosely formulated) plan.

Fly to Toronto or Chicago. Ideally Toronto, so I can meet the Ricardipii clan. Then I'd like to hire a car, and drive over to Chicago, maybe to meet anyone around there, before heading south to a friend in Indiana. Then another trip south, hopefully this time to spend a pleasant evening in the company of Debi, before heading down to the deep south (pick-up at the ready!) to Joy. Finally a night or two with my sister's in-laws in Atlanta, where BLS and Cuz'n Doug will meet us. We'll dump the rental there, and get a lift back to St Pete where we'll spend a nice few days sunning ourselves.
Then we'll do something completely hatstand. Getting a lift to Orlando, we'll catch the train (!) to New York with our own little cabin. Overnighting in New York, we'll rise stupid o'clock to catch a train back to Toronto. This stage of the journey has been priced. In the UK, as most of us know, the trains aren't cheap. The service is crap. The timetable is pointless. This means that I thought it would be nice and reasonable to take this long journey.
$774.50 is not reasonable. $774.50 is f**king expensive. But, like I said, this is where you might have ideas. I'd like to do it around spring time, so March/April/May, but obviously avoiding Easter. Please, comment away.