Thanks for the great ideas so far. I have seen guys with about 3'6" of draft launch from a trailer at the ramp nearby. I think 4' might be difficult (Contessa 26). The NorSea 27 looks interesting. Any idea about how many are aft cabin vs. aft dinette, and availability in the Great Lakes area?
It looks like most boats of this size have deck stepped masts, and if they don't have tabernacle plates something could be fabricated that would allow raising mast without the use of a crane.
I might have trouble towing some of these with my Jeep (5000# max). Maybe I should get my daughter an old F350 pickup for her 16th birthday.