Re: Old but New
Welcome aboard Vinnie.
I'll go ahead and name a boat brand, just because you're probably at the point that you'd like to stop by a brokerage and do a little window shopping. And, a little fantasizing.
Catalina. They've been around about the longest. Made the most boats, and are still making them. Always available used. Whenever someone compares boat brands to cars, the comparison falls apart pretty quickly, but it's probably pretty safe to call a Catalina the Chevrolet of sailboats. I'm NOT suggesting you buy one (although I own my second Catalina right now). Just throwing out the brand as a benchmark. A Catalina is good enough. A middle of the road, decent sailer, designed to appeal to the masses. If you're poking around the brokerage at all, check out the 30, 310, 320, 34, and 36, etc.. Again, before my fellow forum members beat me to a pulp, I'm just mentioning this brand so you, a sail-newbie, can quickly get a sense of what a "good enough" sailboat looks like, what the accommodations are like, and what it's priced like, without making it confusing.
Beyond that, you're going to encounter a vast array of sailboat brands from production, high end production, semi-custom, and so on. Compared to power boats, there are very few mainstream production sailboat brands currently in production. Just a handful.
Other production brands (mostly no longer in production) that are good enough or better, without trying to give you an exhaustive list are:
Pearson, Hunter, Island Packet, Ericson, Islander, Beneteau, Morgan, C&C, Tartan, O'day, J Boat, Cape Dory, Sabre, Pacific Seacraft, Cal, and on and on. Within this list, quality varies, but I've stayed away from ultra ultra high end, and all are cruising boats with the exception of J Boats which produces fast cruisers and racers. I've left out a lot of boats either by accident or on purpose, and my detractors will never know which. So, if you're poking around the brokerage, or the listings, and you see one of these boats in a size you like, it's probably a viable choice (always assuming condition, condition, condition).
Hope this sailing thing works out for you. Those of us who enjoy it as our lifestyle don't have the words to tell you what it means to us, but hope you enjoy it as much as we do.