Hi Diligence, I'm chasing after my dream of cruising also. I don't have anywhere near the hours you have on small boats but I do have a healthy love and respect for the sea. I learned the basics of sailing (meaning I know how to get myself in trouble) by crewing with a friend on a Catalina 27 in San Diego. Since then I have purchased, enjoyed, and was forced to sell my first sailboat, an Endeavour 32. Even though I sailed on Kentucky lake and not the ocean, I learned a lot about sailing and more importantly, what I personally need in a boat.
Sailboats come in all combinations of hull shapes, sail rigs, and accomodations. I would definitely suggest sitting down with your spouse and make a list of what you expect to do with the boat and where you plan to do it at. Will you live aboard? Coastal cruising or circumnavigation? Occasional cruises or extended trips? I'm sure you can find a boat to fit your requirements but it will help tremendously if you can better define what those requirements are.
As far as learning to sail, yes, taking classes will definitely streamline your learning curve. I wish I had taken classes but my income wouldn't allow me at the time. And by defining the type of cruising you want to do, it may help you decide what type of classes to take beyond learning the basics. If there are no schools in your area, talk to some of the sailors at the marinas near you. Perhaps you could learn as I did, by doing. Surely someone out there is looking for an extra set of hands to tend a sheet!
Be careful though. Sailing is addictive. I was hooked the first time the sails snapped full of wind and the boat heeled over and took off with only the sounds of nature in my ears. I burned the lake up last year, my anchor rode was wet every weekend, and I only burned 9 gallons of diesel all year! No saving up for gas money.
Good luck to you!