It really depends on the size of the boat. If it's over 25ft, I'd hire a marine surveyor. The stress factors on a sailboat are much different than a powerboat. You need to be concerned with delamination and blister, although blisters on a trailerboat aren't that big of a deal. Also, I don't think I'd want to start with a 22ft sailboat as my first. They aren't point and shoot like a powerboat. A few systems I'd be concerned about:
Hull, chainplates, rudder, keel, electrical system, running rigging, standing rigging, steering systems, electronics and finally engine. You also need to be concerned with the condition of the sails. They stretch over time and once they lose shape, they dramatically lose effificency. Not to be arrogant, but if you've never sailed, chances are you won't know what to look for--it just takes time to develop the eye.
I have sailed everything from a 12' sailing dingy to 35'+ offshore cruising sailboats...(I still love the cats). My last boat was a Catalina 30 tall rig. I would agree that Catalina makes a very solid boat with systems that are super easy to understand and maintain, plus the support network is huge in the U.S. I too agree that some lessons wouldn't be a bad idea. You might find you just don't like it or the amount of work involved.
FWIW, I've been doing this for 45 years and soloed first when I was 10 or 11. Monohulls and Cats, sloop, cutter, ketch, tried them all.
Way more rewarding that pushing a throttle in my opinion.
Good Luck