So, we sold the Sea Pearl Tri. Oddly enough it was our 3rd one (club dynamics/sailing area) and the new owner's 3rd one too. Delivering the boat to Chiefland, FL Saturday and plan to start tire kicking next week. We are going to slip the boat at Harbor Town Marina on Lake Allatoona and trailer sail once or twice a year for 5 - 10 days at a time. Two strong candidates out there on the market. A 1993 Hunter 23.5, yes we owned one of those years ago (Saint Somewhere), did a BEER Cruise on it and pulled it up and down the Gulf Coast of Florida for 5 or 6 years. Problem is the PO and the PO, PO. Neither were sailors, the current owners kept the mast and boom in their barn and original sails in the house. They kept it at. marina the first year and just sat on it to drink, eat, and listen to music from the band playing in the marina bar on Lake Hartwell, GA. They know nothing about the trailer/boat/rigging/etc. The Previous, previous owner was a doctor who they said did a lot of motoring, but at least he had the mast on it. It also has the original single axle Hunter trailer with the painted axle that rusts from the inside out, as I found out with my Hunter trailer and replaced it with a nice double axle trailer with brakes. The second boat is in the water at Harbor Town, 2003 Catalina 250 WB. The british couple that own it are the second owners, they bought it in 2006 and have had it since. Trailered it a few times and had the bottom done quarterly until the last couple of years when health/lethargy/travel kept them away. It's got a double axle trailer with brakes that has been sitting outside for a while. I'm leaning toward the Catalina. We were sitting in one at the St Pete Boat Show in 03/04/05, I can't remember, and liked the boat. I think the price scared us off. We still like them, but the 23.5 is like a favorite pair of boat shoes, comfortable. Looking at the specs there doesn't seem to be a lot of differences in them except ballast; 1000 Hunter and 1200 Catalina. Prices are $6500 for the Hunter and $9000 for the Catalina. I've owned a fixed keel boat and did not like the way it sailed, maybe it was me, but I prefer water ballast for numerous reasons.
Just reading your post it sounds like you are tending heavily towards the Hunter. Catalina makes great boats. If the Hunter's rigging and sails are up to snuff, and the hull hasn't been abused, sounds like you want someone to reinforce what you already know. As for the price difference, you may be able to replace the trailer with another new one for about that, maybe a little more.
Ed, Practical Sailor had a review on the Catalina 25, mostly favorable.
https://www.practical-sailor.com/sailboat-reviews/sailboats-21-30ft/catalina-250
One criticism I noted was:
"However, he discovered it's a nuisance to tack by himself, since the jib sheet winches are nowhere near the tiller. To tack, he has to abandon the tiller, move to the forward end of the cockpit, uncleat the lazy sheet, pull it off the winch, then move back to the helm before the boat strays too far. When it has passed through the eye of the wind, he again leaves the helm, grabs the new sheet, gives it a couple of turns around the new sheet winch, then trims. This activity isn't helped by the fact that (A) neither winch handle can be cranked through 360 degrees without crushing your knuckles against the nearby lifeline stanchion (which is less than 9″ away from the winch centerline), (B) the jib sheet lead runs from its winch to a Harken cam cleat, mounted very close to the winch drum, and (C) the lead from the cleat runs across the boat, rather than aft."
Work around that and you should be OK.
They also had a review of the Hunter 23.5:
https://www.practical-sailor.com/sailboat-reviews/hunter-23-5
Seems to me, your REAL decision is: the Devil You Know, versus the Devil You Don't Know! :P
Hope this helps,
Charles Brennan
Decisions, decisions... Not sure I can help much. I'm selling my Hunter shoal draft 18.5 for a Hunter 19 WB. Funny - we looked at a 19 in '04 and liked it but thought it was too much money. Hope it's not too late to enjoy. I bought a Mac 26 instead so I have experience with WB. We'll see how it turns out.
BTW: thought of you this past weekend. I passed within a few miles of Ball Ground on the way over to Lanier. I decided to take the scenic route from Chattanooga rather than deal with Atlanta traffic. Was a little wet but I enjoyed the drive.