The continuum of boat ownership through life
Tom, you don't mention how old you are, which I think is relevant factor in the equation leading to "Which boat?" The stage of life has a significant impact on which boat will fit your lifestyle... and don't forget, the boat chooses the captain, not the other way around!To make a broad, completely unfair generalization: the older & more upwardly mobile the sailor, the more boat with below-decks amenities he/she needs to be comfortable. To bring it back more specifically to you, if you are not an AAPR-er, I don't think you need to plan on dropping $25k into your first sailboat. (I write this with all due respect to our age-challenged e-fleet members!

)We're in our 40's with 2 pre-teens. Our 23.5 is perfect for us. A pair of couples in their 20's or 30's? As long as you are good friends -- and not averse to roughing it a little, as you have indicated you are -- the 23.5/240 or the 26/260 would be a great boat for taking the plunge. The 23.5 and 26 have the advantage of being essentially the same boat as the newer models available at a significant discount, so if sailing doesn't turn out to be your "thing," you're not stuck with a $25k white elephant in the backyard.By way of illustration, I think our experience is a fairly common one. We started 4 seasons ago with a 1981 Sandpiper 565, a drop keel 18.5' boat designed to Lloyd's standards to sail on the English Channel. The design was subsequently leased to CL Boatworks in Canada, where you can still find many of them. She's a simple, seaworthy boat -- not a greyhound, by any means -- great for an entry-level situation. Moreover, we got a GREAT deal on her & sailed Shortstay for 3 seasons, during which we confirmed that we were a sailing family. Right from the start, however, I had the Hunter 23.5 in the back of mind (for several reasons, not least of which is an emotional tie to the old Hunter 18.5 I sailed with my dad) and had been tracking the resale market. Before last season, we stepped up to the 23.5 because we found Shortstay just wasn't big enough for our growing family and, more importantly, the broader horizons we explored as we felt more confident as sailors, ready to take on longer voyages. So that's how we've evolved.Looking further down the road, we may some day move up to a larger keelboat, but living in the mountains of Vermont, trailerability is a key factor. I actually have my eye on (like the wanderlust of an unfaithful husband, you never stop thinking about the "next boat") the Telestar 28, a trailerable trimaran, but there's no way I'm sinking $60k+ into a new boat at this time in my life. I'm hoping by the time we're ready to step up -- if ever -- the resale market will have brought this boat into our price range.Apropos of the other advice, yes, the local club will be a significant asset/resource as you start to climb the learning curve(s). As long as it's not prohibitively expensive, it would be a great investment in your seamanship, safety & enjoyment.Also, there isn't a boatyard in the world that doesn't have more than a few beautiful lonely boats, pining away in dry docks for several seasons, waiting for someone to come love her again. This is relevant not only for finding a "good old boat" at a great price, but also a cautionary tale about jumping in a little too far, too fast, only to find out you don't have the time, money, crew, experience, etc. to actually use her.That said, I'd heartily endorse you go out there & get the keel wet this season! Let us know how it comes out.Kevin FitzpatrickBrownsville, VTs/v GrasshopperHunter 23.5