I used to be one of those sailors who believed deeply in racing ... other people’s boats, especially when it came to big boats. Racing your own boat seemed like such a hassle (organizing and provisioning for lots of crew), as well as a potentially voracious, money-sucking, black hole (new sails, bottom jobs, and divers, just to name a few). So the biggest boat I ever owned and raced was a J/22. Even that was downgraded to my current race ride: a Laser. And I was content.