My experience was as follows:
Wanted a 30+ foot boat for sailing on Lake Michigan. Wanted a diesel, and wheel steering.
Found a 1988 O’Day 322 that I fell in love with. For sale at $29k. Sold before I made an offer for $25k. Nice shape.
Bought the next boat I looked at, a 1996 Hunter 280. Great shape. Turned out to be a great first boat. Owned her for about 4 years. No major issues, just regular maintenance items (oil changes, bottom paint, etc. ).
Then the guy who bought the O’Day 322 (out from under me I like to say) emailed me to tell me he moved, the boat was still in Michigan, and “make me an offer”.
I knew what he paid for it, and he added a chart plotter, so I offered him $22k. He took it, and I owned 2 boats for a little while. Luckily, sold the Hunter before winter storage time!
Have owned the O’Day for several years now. Now major issues, but I did replace my prop shaft, cutlass bearing, coupling and stuffing box hose (prop was original bronze and had a crack in it).
The O’Day 322 is a much heavier, seaworthy boat. Much better cabin (full galley, larger head, bigger berths.). But the cockpit is actually smaller.
My goal was to have a boat I could sail, not one that I had to spend all my time working on. I could afford a bit more boat than you are considering, but be careful...as others have said, repairs to an older boat that has problems may cost a lot more than the boat price.
My “fleet”: Hunter 280 (R) and O’Day 322 (L).
Good luck on your decision.
Greg