Trailerable sailboats have undergone a major change in design in recent years. It's getting increasingly difficult to find a good, used tow vehicle with a powerful engine, so manufacturers are finding ways to build lighter trailerable boats that can be towed by less powerful tow vehicles. Older 25' boats, like the Catalina 25, which is a very nice boat for its size, are heavier, and that weight not only makes them harder to tow, but it also makes them harder to launch and to rig. The newer design Catalina 250 is lighter, and easier to tow, launch and rig.
Also, within this size range, a relatively small size difference can make a big difference in the boat's weight. A Catalina 22, for example, can be towed by a mid-sized suv, and can be launched and rigged by a single person, but a mid-sized suv can't tow a Catalina 25, and it is much more difficult for one person to launch and rig it. (although it can be done with the necessary rigging.)
The bigger, older boats have nicer interior accomodations and generally sail better, but, unless you plan to keep it in a slip, you'll find that you won't sail it very often, because it is so much work to tow, launch and rig it.
So, if you plan to trailer-sail, then you should either look for a smaller, older boat in the range of 20-22', or a newer boat up to 25' with a more modern, light-weight design. If you plan to keep it in a slip, you can luxuriate in a bigger, heavier, older boat.
When you're buying real estate, the 3 most important concerns are location, location, location. When you're buying a boat, the 3 most important concerns are condition, condition, condition. I've seen many old racing boats in superb condition, and visa versa. The same is true of cruising boats. It isn't about how they're used. It's about how they're maintained. It is true, however, that you have to look more carefully at old racing boats, because they're designed and built just strong enough to withstand the stresses, and no stronger, and because the've been subjected to maximum stress much of their existence. But, people are still enjoying good old J24s, Capri 25s and similar racers just as much as their fathers did, a generation ago.
Don't be in too much of a hurry to buy a boat. Look at a lot of them. Volunteer to crew on different boats, so you can see for yourself how they behave.
I learned to sail a boat with a tiller, and, although it might sound a little fanciful, I liked to think that the boat "talked to me" through the tiller. Whenever the boat started to labor, it became apparent first by increased tiller pressure. When I felt too much tiller pressure, that told me to start looking around for the cause, to optimize the boat's performance. Sometimes I could reduce the pressure by increasing the tension on a sail control, like the traveler, or a halyard or outhaul or backstay adjuster, or to make some other adjustment. When the tiller pressure started to lighten, that told me it was time to start thinking about easing all the sail controls. My present boat is a 35 footer, and has a wheel, and I've learned to like it too, but the wheel doesn't talk to you as clearly as the tiller. If you'll learn to listen to what a tiller is telling you, I think you'll be a better sailor for it.