I've sat quietly through all of this, and I'll say that you've completely crossed the line of being a "thoughtful, and frugal shopper" into total paralysis.
You've built a list of impossible-to-satisfy criteria, along with the equally impossible criteria that this entire
list must be satisfied. It seems that you're more in love with the idea of boat shopping, than boat ownership or any actual sailing.
I recommend that you sign up for a fractional sailing membership, like www.Sailtime.com
, and spare yourself the agony of "should I or shouldn't I?" This way, you can enjoy sailing without worrying about surveys, re-sale values, and all the other stuff you're worried about. It's guilt-free, responsibility-free and as low-risk as possible.
I understand your desire to make a smart purchase, but your insistance that all
risks be 100% eliminated, and that the boat perfectly conform to your fantasty, is unrealistic.
You have made "perfect" be the enemy of "very good" for the express purpose of sabotaging your boat purchase. That way you're safe, because you haven't made a mistake.
You'll pop up here every few months, for years, with some new boat that you're looking at on Yachtworld, asking the same advice over and over...but you'll never buy a boat. You'll always have a perfectly good reason not to pull the trigger. Something won't be perfect enough.
Once more, for the record:
I applaud your desire to make a smart purchase, not rushing headlong into a project, but you're paralyzed.