Thanks for all the advice. So I guess the Oday is a better bet. just as an example of what I was seeing between 1000-2000 check out this Mcgregor:
I can work with wood/metal/fiberglass pretty well. I have built a couple row boats and a cedar strip under glass canoe. I am just trying to strike a balance between "ready to go" and free empty shell where I can get out on the water for as cheap as possible. I found a ~1975 22' Oday that is basically a soild hull, standing rigging and decent sails for $1000 but it needs paint, interior and running rigging.
The catalina looks ideal but I haven't seen any that cheap yet. Definitely will keep a look-out. My plan would be to keep the boat in the water all season and only trailer to and from my backyard each year. I am wordering if I can get away with renting a trailer and borrowing a truck.
Anyways, if there are any more opinions out there I would be happy to hear them.