I know this is a few weeks old, but I wanted to just throw in a couple comments anyway...
My boat, 1990 Hunter 27 fits all of MStern and the OP's requirements:
1. Big cockpit
2. Head behind a door
3. Less than $10,000
4. Sleep 4-6
5. comfortable cruiser
6. Fast as can be reasonably expected from a 27ft boat.
7. Affordable maintenance (It's an 8HP outboard)
I can comfortably seat 6 in the cockpit, as well as sleep 6 (as long as one person is not too tall), and even squeeze 6 in around the settee. Seperate enclosed head, paid $8k for it in very good shape, bought it from the original owner.
As for speed, with 4-6 people on board I can routinely hit 6+ kts (LWL is 22.3ft, theoretical max speed is 6.3kts), and do so on most tacks in as little as 8kts of wind, depending on which sails I have hoisted.
The only thing that I can't comfortably do is single hand the boat, and that's 95% because it has hank on head sails, and I don't have a wind vane or any sort of autopilot (or even a tiller keeper, but that is on my to do list).
all in all I am very pleased with my boat, it was just a year ago that I was making the same decision as the OP Mike as what was a good boat to have on LIS, and had the same list of requirements. The only difference is that I didn't buy the boat expecting to race it (although I'm considering doing so this season.)
Four Points - 1990 Hunter 27'
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