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wrote:
snip
-I am also looking at C&C 38 Landfall (nervous about older hull and
deck) and Freedoms in the 36' range (nervous about hull)

Get a pre-opec C&C and all will be good. As to the other stuff, you're
stepping up 2.5-3x the weight you're used to. Inertia! Respect it.
Any 15000lb boat that starts getting sideways on you in a crosswind is
not going ever going to be easy to deal with on your own. Nice boats?
There's tons. Old Allied Seabreeze's, not particularly quick but
beautiful and they'll take you anywhere. Hinterhoeller Nonsuch models
are built for single handing, are cavernous below and hold their value
very well. In fact any Hinterhoeller boat is worth buying.