A Vancouver 27 will safely take you round the world if you like, a very tough cutter-rigged, long-keeled yacht with stowage to match a much larger vessel:
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I've had my 1982 example for 12 years now, sailing up, down and across the Channel single-handed or two-up.
Two words.
Albin Ballad.
That looks well alright, especially for the price. I haven't logged on to see all the photos (stupid BoatShed trying to harvest emails!) but it'll get you going and give you heaps of primary experience. With care and understanding a late 80s engine might well last a few years more - and give you more experience still! Once you've got some sea miles under your keel, you can then decide whether to invest more time and especially real money in bringing her up to snuff, or move her on and buy a different type or size of yacht.
I don't think many would choose a 26ft boat for the kind of stuff you have on your list ross. The good news is that I don't think you need to go that small to get yourself a very useful boat - provided you are willing to do stuff yourself.
Rivals have been mentioned but check this Sadler 32 out:
https://www.theyachtmarket.com/boats_for_sale/1749894/
It looks in nice order, asking just under 13 grand. This would leave you room for new sails if needed, plus the other bits as required. Don't look for the perfect boat, look for a good one at the perfect price.
Thx. Fake email reveals a boat that looks only superficially manky (i.e. not properly cared for in the last couple of years or so) and so should scrub up pretty quickly with human muscle rather than too many readies.
Anything needing overhaul will reveal itself quickly and give the OP much primary experience in the usual myriad of boat systems. A can of deck paint will easily brighten the superstructure.
With the long keel, rudder hinge at that traditional angle and the small aperture for the prop, she won't go astern with any predicability of direction whatsoever. But the OP can learn to warp her around pontoons and docks, and once he's sussed which way the prop kicks in astern he can jam the tiller over hard and by working the throttle forward and astern he can practically turn on a sixpence.
Offer an initial £3,750 subject to survey, including running the engine (if ashore then just plum in a hose), and maybe get a local boat electrician to give the electrics a quick once over.
Perfect price for the buyer! I think I spent nearly that much on mine last year alone. Just goes to show the importance of buying one with a newish engine. One of the big differences between 26ft and 32ft is headroom
... Offer an initial £3,750 subject to survey, including running the engine (if ashore then just plumb in a hose), and maybe get a local boat electrician to give the electrics a quick once over.
The baby Bowman isn't that bad actually, but then I had an Albin Vega for a couple of years...
When reviewing boats to ascertain their value to you, I'd start off by making a spreadsheet. List every item of "Key" equipment you want to be up to scratch before you cast off to go transatlantic.
For instance;
Running rigging <5 years old,
Main Sail <5 years old,
Foresail <5 years old,
Second foresail,
Storm jib,
Drogue,
Standing rigging <7years old,
Electronic Autohelm,
Windvane self steering and so on.
Then spend a little time pricing all these items up by trawling the various online chandelry.
With a little formatting with tick boxes and formula's you will be able to quickly ascertain a high level upgrade cost for each boat you look at. With this you can then compare the "value" to you for each and every boat you look at. It's also easy enough to keep a copy of this spreadsheet, with online info from advert, correspondence with seller/broker and any photo's you take in person altogether in one note.