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From previous posts I think I have a gist of what you are after and a S23 with all its compromises will fit. What I am not so convinced about is once you have sampled cruising and over weekending that your priorities wont drastically change. Which is fine, but lets be honest, you dont sell to upgrade, you have more boats than you can shake a stick at!. My concern would be you'll end up with too much of a compromise for you to really enjoy her. So if you do plan to continue buy once and keep Id urge you to reconsider something in the 28 and above class
It also depends on your family.
When we had the S24, a weekend aboard was fun at first (when we were a lot younger :ambivalence because life afloat was a completely new experience.
We then found that the novelty wore off, and having a bit more space became a priority.
Interestingly, upgrading to the SC35 has not increased our time onboard or cruising range vs when we had the S28, hence my comment about there being a "sweet spot" in sizes.
Two engines and a bit less than 30ft, you can go almost anywhere.
Okay, maybe not Biscay.
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