A boat that size I think it really does not matter what kind it is, it is all about condition. It is not like the investment is so much (I know most around here are not made of money, but we are not talking mortgage) if you are not happy you can turn around and sell it for at least what you paid for it. Likely you will want to move up anyway, unless this really fills your future plans.
Spoken like a person who hasn't tried to sell a 4ktsb lately.
Yeah its small money paid. Yeah everything else he said is correct (it's only money)... however, selling an older boat even at cut-throat prices, can sometimes take a while (measured in months if not years). There just isn't a huge market for small sailboats. Given how long I've seen boats listed on yachtworld and sailboatlistings, I'd say it's not a huge market for pretty much ANY sailboat.
With that the suggestion of a Catalina 22 is a good one, in that they are very popular and are generally easier to sell then some of the lesser known brand boats. And Catalinadirect is a great source of parts for anything Catalina/Capri.
But if you really LOVE the boat, and the condition is what you like... then get it. One's ultimate decision shouldn't JUST be about what the thing is worth when you want to rid yourself of it.
Be familiar with what it takes to rehab a swing keel (they nearly always need cable/pivot pin work). Also the trunk can sometimes have some minor crazing and worse damage.
Like all boats, look at chainplates, gudgeons, pintles, hatches, through-hulls, and thump the hull for soundness (thud is bad, thwack/tap sound is good). Look for rotting bulkheads. Look for osmotic blisters... Check the mast step (is it square, and flat?)... Pulpits, and stanchions, check for bends (if bent check the deck underneath for cracking or leaks). Check the bow eye (look inside the boat), last 3 boats I've bought had damage to the bow-eye (some monkey probably thought the boat could be lifted from the bow eye).
A trailer is involved, so look at the BACK of the tires (where most dry rot is prevalent)... jack up the wheels, spin them, listen for marble in a coffee can sound. Inspect the brakes (if it has them - pull a wheel)... check the actuator (again if it has brakes). Check the ball clasp. Inspect the safety chains. Test the lights. Check the trailer winch, and strap.
I could go on for days about this stuff.... NONE of it is a game changer, but put time/money/hours to each of those repair jobs, add it to the listing cost, and ask yourself if it was fixed/repaired is the boat "worth" that kind of cost to you.
My last 3 boats cost me about 20-40% more in repairs the first year I had them, and that didn't even include sails.
Which leads me to "sails." I LOVE these "sails are OK, or crisp" statements by sellers. Yeah but how OLD are they? Most times they are original! My present boat sold to me, had 18 sails with it. the NEWEST sail, was 2006. It was used for 2 seasons and stored inside. It's probably got about 2-3 more seasons for racing in it... The rest of the sails? 2 original sails (main and 110 were in decent shape, with little use), every laminate sail and there were 5, were FOLDED, and stored, and the lamination blew through on the folds. I DID however, have probably 5 spinnakers with nearly each being in decent and usable shape.
My point? PULL THE SAILS OUT!!! they are a HUGE expense (even cheap sails are pricey). Look for stretched (shrunk actually) boltrope on the main (means the sail has been overstretched/wet many times and then sat on a shelf a while to dry/shrink)... look for tears, pulled seams, batten pocket damage... these are all signs of "abused," sails. On a 22 foot boat, you are looking at about $700 for a cheap NEW mainsail. Probably same for a 125% genoa.
Also outboards are a huge sticking point for me... boat without motor? Ugh... you'll want at least a simple motor (2 stroke with integral tank)... those will run you about $300-$400 used, and will need some work usually to keep running right. New? Forgetabout it, more like $900.
So add up the headaches, put a dollar number, and number of hours on it, that will be required to get the boat/trailer/sails/motor, safe/functional, then you'll have a pretty good idea of what the boat really costs.
Congratulations I just made you a small boat inspector.