Sorry not new to sailing but new to forums,

Hi Dave
I was working one year in Milwaukee in 2000. Boats were already give away prices.
I star planning a passage.
All boats around Lakes are out of water in winter.
Just to get to East Coast must be great adventure.
You can leave spring but half way going south along east coast you in hurricane season.
You wait or risk it and sail and hide. I visited many place from N.Caroline
to Key West, wouldn't see any hiding places, just exposed marinas.
November is still hurricane season in the Atlantic.
East coast and Caribbean in a rush to make to Panama around January
Leaving Panama for Galapagos is usually done in mid to end February.
Than by October back in OZ.
Perhaps with good crew and race to Panama
before hurricane season and than you have to wait anyway.
West coast would be smarter option to buy the boat . That's my opinion.

For the adventure I guess!! Yachts are meant to leave the Marina.

Just reading from Kindle a book .... James Baldwin "Across Islands and Oceans"
No idea about sailing bought a Pearson Triton 28 on Gr. Lakes and sailed through East coast, Panama around . And sail well. / not ones /.
I personally wouldn't miss East coast, from Cape Hatteras to Key West, simply paradise,
ocean crystal clear, boiling hot and hundreds of spots to drop the anchor every night and discover.
All because of the Gulf and dozens of Outer Islands.
Hurricane season June to November. Sailing window from Panama to AUS Feb. to Oct.

Go Dave ! I am jealous as hell . I did a similar trip a few years ago. should work well ,hurricane season getting ready and out of the lakes to NY and down to Chesapeake bay then November to march getting to panama ( or get there later (june)after doing the carribean and spend the next hurricane season in panama as it is out of the danger area and heaps to see/do)
Then April to oct in pacific .in a perfect world hole up somewhere like tonga for the off season and go again next year it's a bloody big area.

Rather than listen to me get a copy of jimmy cornells world cruising routes and start planning!

If you are interested and end up going that way pm me I may have a pile of charts and guidebooks for sale