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$.02
With your budget, I would go into the 30 + range as the comfort level would be better for a family of 3. On the low end of the price range there are many very good boats, but they will lack amenities like hot water, shower, refrigerator. If you go that route good 70's boats would be Catalina, Ericson, Cal, Endeavor, O'Day. If you go older anc cheaper you may end up with an Atomic 4 for powere, which is a good engine, but it is gas. I would avoid any other brand of gas engine as parts will be a problem.
I kind of like the Endeavor 32, which you could get with a diesel in the low to mid 20's. It is a decent sailor, well built, comfortable, and has room for 3 people. I owned it's relative, Irwin 32, (same mold) and found this to be a great boat. Endeavor is much better constructed and is suitable for some offshore sailing according to Practical Sailor.
Upwind is not the boats strong point, but that is typical for this era. Off the wind in a breeze it will move nicely. Light air would not be the boat's forte, but she will be good in heavy seas.
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