Jeff, grow into it
Jeff, many have suggested the same strategy probably because that is what we have all done. Start small and as your skills and comfort level grow, trade up. I learned on a 22, bought a H29.5 and just traded up to a H356. The H29.5 was a fantastic boat for us to really get the feel of what lfe abourd would be like. We travel the Chesapeake too, and have spend many week-ends and a week here, week there type of vacations. The 29.5 for the two of us and dog was perfect. The boat and setup was perfect for singlehanding when the admiral read or napped and it allowed me to learn about boat electronics, electrical systems, diesels, etc while I improved my sailing skills and gain confidence. IMHO if you start with a real large loaded boat with all the bells and whistles, you get overwelmed (and possibly financially frustrated) because of all of the complicated systems on-board that need looking after.
Jeff, many have suggested the same strategy probably because that is what we have all done. Start small and as your skills and comfort level grow, trade up. I learned on a 22, bought a H29.5 and just traded up to a H356. The H29.5 was a fantastic boat for us to really get the feel of what lfe abourd would be like. We travel the Chesapeake too, and have spend many week-ends and a week here, week there type of vacations. The 29.5 for the two of us and dog was perfect. The boat and setup was perfect for singlehanding when the admiral read or napped and it allowed me to learn about boat electronics, electrical systems, diesels, etc while I improved my sailing skills and gain confidence. IMHO if you start with a real large loaded boat with all the bells and whistles, you get overwelmed (and possibly financially frustrated) because of all of the complicated systems on-board that need looking after.