Re: Cat 25
My first boat was a 1984 Catalina 25. I bought it almost immediately after taking sailing lessons.
It was a nice boat to get into sailing with. It sails quite well and the tall rig was good in the light air that we have in Seattle. The boat is pretty forgiving of mistakes which makes it suitable for learning on. It's cruiseable and raceable, more so than many other 25' boats which are trying to only do one or the other. It's not great at anything, but it is good at almost everything.
I like the simplicity of the systems on the boat. An outboard engine, basic head, manual pump water, simple electronics, and transom hung rudder are all robust designs that are easy and less expensive to maintain.
The 1983 and later ones have some design features that make them a better choice than earlier models. The fuel locker is a safer design, heavy hardware was properly balanced to keep the boat level, and minor upgrades were made throughout the boat.
As with any boat purchase the most important thing is getting a good one. Even on an inexpensive boat you'll either want to learn how to survey the important stuff yourself (most importantly checking to make sure that the hull and decks are solid) or pay for a survey to be done. A Catalina 25 for $2000 that needs new sails, motor, cushions, rigging, and deck repairs is no bargain compared to one for closer to $10,000 that has been well loved and where all of that stuff has been replaced in the last couple of years.
boats that I sail on regularly: Pearson 28-2, Rondar 505, Yankee 30, Blanchard Junior