If it were me, I wouldn't go for ANY of the boats on the list above, there are LOTS of better boats for what you want to do, in your price range, and within a reasonable distance. Not a big fan of boats on Craigslist, they all seem to be Tired and the fact that its a free listing for everything and anything, IMHO makes it a bit of a Dumping ground...some better websites like Sailingtexas.com or sailboatowners.com will reveal MUCH better smaller boats. Like Cheechako said above the Chrysler's are real good boats that are often overlooked, also the Rhodes 22.... and your 1500 can probably haul anything up to 26 feet at least. So don't limit yourself as far as distance.
Another bit of advice: I would be leery of a boat with no real and current
pictures of the interior... There's probably a reason they dont want you to see it... and down here in the Deep South, its liable to be a Mould and Mildew Farm down below. about 8 years ago, we drove 3 hrs to ATL and looked at four brokered boats on Lake Lanier with good looking photos... in actuality they were uninhabitable, and in serious need of gutting to the hull
to get at all the mould!
so dont trust a broker to necessarily represent the true condition. (no offense to brokers here, but it was my experience) The Tanzer is a good example of this: No real description and misspelled, the interior is all flipped up, and a bottle of jim Beam in the Galley
...really, Mr Broker, REALLY?
Ok, enough of the soapbox....Back to the question...
If pressed, though, I'd go with the Catalina
1st, Because of the support and they are still being built (but I would look for a regular C25 not a Capri, the Capri is more of a racer
, unless thats what you want to do), then maybe the O'day, but you will want to get a newer outboard, and check the bottom out really well. The Tanzer would be next, I have heard they really were fantastic little boats and if she's been loved then she might be ok...
I'd be suspicious of the others...the Ticon looks ok, but the "Partially refurbished" thing says "un-finishable"
and the Santana has no real pictures of the boat, But the open transom, and vey short cabin
top scream "race boat"... probably not going to make the wife and kids
happy on Cruises.
next, the Macgregor
...$6800 for a '92 Macgregor
S...??? BWAAAA HA HA HA!!!!
and only, ONLY take the Buccaneer if you get paid to take it to the dump, That boat is one very well polished turd...dont even THINK about paying for that thing.