The Benford designed boats are really interesting. They're dories, so they have a flat bottom, which seems daft, but under sail when they heel over, the chine presents as a "V". You can put either a full keel or a wing keel, or I think I've read that twin wing keels work as well.
Annie Hill has a book, "Voyaging on a Small Income" that talks a lot about their Benford dory "Badger". The layout is really smart, it doesn't try to jam in 9 million sleeping accomodations, the galley is large, and there's a ton of storage.
And with the junk rig, it's really easy to build, maintain, and repair yourself. Blondie Hasler (mentioned in the For Sale ad), put a junk rig on a Folkboat, which doesn't seem sane, but he made it work. The design of the junk rig is very forgiving of not-very-precise sailmaking. Reefing in a blow is particularly nice, as you don't have to struggle with it. The weight of the battens just naturally let the sail drop.
Plastic (fiberglass) boats can “last” (continue floating, at least) a very long time. But they can go from well-maintained and usable to immobile and dangerous in months without attention.
Source: owner of a 45-year-old, well-maintained sailboat (not my first).
My operating costs for a 38' are around $10-15k annually, including a slip at a (low-cost) marina and maintenance, but doing most maintenance myself. The first year had at least $10k more in "catch-up" maintenance items. I do pay others to periodically haul the boat, repaint the hull, check zincs, etc.
It would be considerably higher paying shop rates for most maintenance, or if you had expensive tastes in sails or electronics.
For me this works out to about 15-20% of the cost per boat in ongoing annual opex cost. Kind of like a software maintenance contract!
* Fixing leaks from things like deck prisms, portholes, deck, chainplates. Usually involves epoxy, sealant, disassembly of components
* Care of interior and exterior wood - varnish, or oiling, or other protection as preferred
* Regular lubrication of moving parts, such as the helm and steering assembly
* Replacement of running rigging (ropes that control sails) when it gets tired
* Checking standing rigging (steel cables that keep the mast up), replacing when needed, though these last a long time. This usually needs professional riggers and is more expensive.
* Keeping corrosion under control - stainless is never as stainless as you want
* Replacing sails every 10-15 years, assuming you are ok with more tired sails toward the end
* Having diver clean hull, also repainting hull every 2 years, replacing zincs as needed, usually 1-2x annually depending on water type
And other stuff. Replacing marine toilet pumps, fixing shower sumps, replacing bilge pumps, fresh water pumps, etc.
These things aren't as bad as they sound if you like working with your hands and have time. I like it because my day job limits the use of my hands to the keyboard. And you don't need to know how to do all this stuff - I learned almost all of it while attempting to do it, and I still learn all the time. But if hands-on work isn't your cup of tea, it will get very expensive.
The reward, beyond the fun of doing the work, is sitting on the deck, anchored at a remote island looking at incredible sunsets in the summer. Or being the only boat out on a winter day and seeing a humpback whale surface near your boat, hang around for a while. Or sitting down below next to a warm fireplace in the winter with a good book listening to the patter of rain. Sleeping on a comfortable bed in absolute silence in remote areas, far away from any cars, sirens, or other people. Trimming the sails and feeling the power of the wind energize the boat, pulling it forward as your boat nearly silently cuts through the water.
For me, totally worth it, but it does become a fairly important part of your life.
