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I grew up living on boats. Lived on Catalina for a while, was a harbor patrolman and lived aboard. First was a 40' sportfish then a 31' sailboat. We just got rid of our mooring at Catalina since we weren't using it anymore. From a maintenance and cost perspective you are much better off buying sail over power. For a single guy I would say the minimum size is 30'. San Diego or Dana Point are both nice. It would be great to get a slip in SD down by the Gaslamp. Stumble back to you boat after a night out! Good luck and go for it, if not you will regret it for life.
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