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I own a CS27 with a Yanmar YSE8 diesel - my 4th boat with a diesel. Easy to maintain - I'm not a fan of outboards. The 27 sounds like the better boat possibly. If it hasn't blistered yet it probably won't in my opinion. It is probably better equipped. As to maintenance differences, almost same length so winter storage, moorage, and bottom paint costs should be similar. Through hulls aren't a problem - the 27 has a few more - if the 250 has a galley sink there should be one for the outlet I think. The 27 will be the better sailer I think as well.
Brian
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