Now, from some of the comments, it seems like the winter storage might consume more time than I expected. I hear "be there by November", and "you can be out by April or May". After doing a bit more digging on weather, once you get up into the great lakes area, the winter time frame gets pretty long, so the boat could be tied up 5 months. Besides, getting out too early, like mid to late March could be freezing cold. I don't want to tie the boat up for 5 months.
I'm rethinking this a bit... and considering a 1 year plan, and perhaps going back to closer areas like the east coast for a summer run. And I'd spend more time on the boat and skip a few travels that I had that would take 6 weeks or longer. Just a thought.
The extended boating season on the Great Lakes is May 1-Oct 15. Most boat a shorter time. What we did on the Loop was ran up the East Coast just in time to leave NYC when the Erie Canal opened. Last year that was May 1. We then used from May 1 to Sept 30 to boat on the lakes and left Chicago on October 15 to head south. Even on that schedule we hit some cold temperatures for brief periods on both the Erie and on the Illinois.