That is a nice looking 38'. If you add it up, that is some nice kit.
Message me if you want to know what we paid and what was included with our 38-200.
For me, buying from a family that was getting out of sailing was a big perk, since we were newly getting "in." So, all their"stuff" came with the boat, which made both parties happy.
I also happen to think getting the absolute best price is often not worth it. Owners that care about their boat want to sell to someone that also shows passion. You want a seller that cared about their boat. Trying to save the an extra grand or two on the purchase isn't really worth burning an open line of communication with the seller. (or surveyor or broker) You will have questions later.
I'd venture owning in the mid-west is as cheap as it gets, and I estimate it will cost $6-7k per year to own a 38' boat on the Great Lakes. 10 years is $70k in "basic running costs." Plus any major items. So getting a boat for $35k vs $37k really doesn't matter. The ten year cost is $105k or $107k.
Either way, you are committed. (and probably should be committed.

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