There are forums
focused on specific boats, like, for instance the Catalinas. The participants address the common issues of the boats -- in their various sizes -- and what they have had to do to bring the boat
up to what they think is serious seagoing condition. Here on CF, there are a few engineers and guys with lots of experience who can answer specific questions, and I bet some of them, or people like them are on other forums
, as well.
Personally, I like Stumble's plan for you. Getting a pair of inexpensive dinghies and sailing the ----- out of them will teach you and your wife a whole lot about sailing. After you've decided you like it, then move on. Keep it inexpensive at first, and then, when it comes to lessons, if it does, you'll have an experience base to build on.
By the way, there are a lot of vets here on CF, if you hang around for a while, you'll be able to pick them out.