Yeah, um outboard, makes life easier.
All stanchions missing? yeah I am with FtWorthSailor, I bet there has been water penetration in the deck. (Silicone) Caulk and fiberglass don't mix.
Cushions aren't cheap (but can be covered cheap, but they look like chair slip covers).
You should look at the sails, not take his word for it. Dirty is easy (woolite in a trashcan), torn is a PITA, missing parts worse.
Cat 22s are notorious for their winch
cable assembly problems (after 30 years)... replacing the winch
, or the cable isn't really the big deal, it's getting the 500lb keel to swing freely enough to work on it, that is.
Sounds like looking around might be in order.
Also on a 22 footer like that, it's handy to get a trailer (even if it's just a yard trailer). Paying for haul outs on a 22 footer is crazy (especially a $700 boat), when you can throw a trailer in the water and pull it out with a small pickup.
Just my worthless $0.02