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"a cruiser/race 27-30ft for 5k-8k USD. Now my question to you is, is that possible?"
I'd say possible but strongly inadvisable. If you can buy that much boat for that much money, you certainly won't get a healthy diesel with it. You probably will get a terribly used A4 or an outboard that someone threw on it to replace a burnt out inboard--which is a Frankenstein thing you don't want to get into.
And, at that price you're probably looking at an old tired boat, even if it is a Pearson26 with the wrong (short shaft, low power) outboard bolted on.
Then there's the main powerplant, the sails. At that price range you'll probably need new sails this year or next, figure $3-4000 for a main and 150 genoa, maybe a bit less ($2500-2800?) at the right time of year for basic dacron.
But since I'm a pessimist, you'd better ask CPaul to come up for dinner and check out some boats with you.
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