In a couple of posts, Lew, you referenced your boat. Sail or power? I used to sail the Chesapeake in a 32' Beneteau until we moved to Wisconsin. Haulers wanted nearly 5K to move it and we weren't too enthusiastic about sailing Lake Michigan. That was six years ago and I still look at the used boat ads every April.
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Ever hear of Jan Guthrie in Racine?
She has a brokerage there.
You are talking to a Great Lakes cruising sailor (Erie) and I highly recommend it.
A trip to the North Channel is a cruise to be remembered.
Had a Seafarer 30 that I sailed out of various ports on the south shore of L Erie.
$5K for freight is a tough nut to crack, especially when you are talking about taking a "saltie" into fresh water.
Lots of 30-35 ft boats available between Chicago and Racine.
As far as my project is concerned, came to California and within a year started construction of "Challenge".
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Lew