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endeavour, hunter, irwin???
I agree with Jeff that your question is still very open-ended. Also that you will get a bunch of opinions from sailors here--each with a different bias.
Personally, I would also second Jeff in that Irwin and Hunter are probably good bay boats, and I''ve sailed on several models of each, but not my favorite for long term cruising. The Endeavor 37 is sometimes mentioned as a cruiser--with relatively shoal draft. Also the older Tartans sometimes got good press, particularly the 34 and 37--centerboards and reasonably well made, 70''s boats.
However, if 50ish is you cost target, the boat itself must be significantly less than that. Systems will probably need to be upgraded for safely, sailing and living: like 406 EPIRB, pumps, wiring, electronics, sails, lines, dingy, spares, bottom paint, anchors: all of which cost quite a bit.
Cruising world did a series of articles in the last couple years on "Vintage Plastic" sailboats with relatively low cost and decent heritage. You might check on those articles. And when you get closer to buying, a surveyor can be your best friend.
And a caveat: everything in this post is just one man''s opinion--the most experience you have with a variety of boats and conditions, the better decision you will make.
But in any event, you have a great idea, and I applaud your desire to go. Go for it!! (Pun intended).