Wow what a great outpouring of responses! Thanks for all of the input and offers.
Here is where I'm at in the process. We finalized the agreement and I accepted the boat yesterday.
The owner has a week to finish a short list of corrections that came from the survey, and they I gave them another two weeks to get ready for their move back to Canada (they have a ton of stuff in storage they need to deal with, etc.). I'll take possession on the 16th.
I would love to make the entire trip home by myself, but I simply don't have enough vacation. Also, my wife and I are anxious to do some projects to "make her ours" and I can't do that if the boat is 1,000 miles away, so I'm less interested in "segments". However we DO have a couple of weeks of vacation that we can dedicate to this, so our goal now is to get it delivered to Oswego where we would take over. We'd spend our time in the Trent Severn, Georgian Bay, and Lake Superior home. That would be a much more enjoyable, memorable use of our vacation than pounding 12 hours a day up the east coast.
I have a very good friend who's an experienced captain (50 Ton Master), instructor, and delivery captain, but his experience is Great Lakes to the NE, and many years in the Caribbean. He's not experienced on the ICW. Given that this is a delivery there will be running inside when needed and outside as conditions allow. I really want someone who's experienced with that part of the trip.
Fortunately I've gotten numerous tips from members here, and several of those are very experienced in that exact route. My current plan is to employ one of those experienced captains for the run from FL to NY, and then hand the delivery over to my friend for the run up the Hudson / Erie Canal. We'll take over from there. I will also join for the first few days as it's killing me already to not be getting to know the boat. Based on discussions with the captain I will add one or more crew.
In terms of dates, I can't really benefit from leaving earlier than mid May. The canal isn't open and neither is my marina, plus I'd rather have it nice for our cruise through Canada. That's no concern however because I'd like to do some upfits to get her ready for the trip (electronics mostly), and it wouldn't kill me if I had to cruise around the Gulf Coast for awhile. So I'll work with my employer to work remotely for a couple weeks in March and April, get her ready, and leave FL around the 10th-12th of May. That should give enough time for the Canal to clear out before her arrival and likely put her in Oswego around Memorial Day. I think that even Canada should be thawed out by June
Once all of that is behind us I'm very much looking forward to getting more "big" boat experience and becoming an even more active member of this wonderful forum!
Thanks,
BD