Re: Smallest boat you can live with
"Live with" for me means being able to spend a summer cruising on it, but not living aboard full time. It should fit a couple comfortably, and two couples for long weekends or some shore stays.
Many boats around 30' meet my performance and cruising space goals. My ideal boat is probably something like a J/35 that is more performance oriented but with the interior space of most 30' boats, but a J/35 would cost $10k more to purchase and $3k/year extra in moorage compared to a 30' boat.
I tried a 25' boat, but not having standing headroom was a real problem for me for cruising longer than a week. There was also a lot less covered storage space than on our Pearson 28-2. Going from a Catalina 25 to our Pearson 28-2 was a massive jump in available space. I've spent enough time on 32-35' boats to know that the next 4' size jump won't feel as large.
boats that I sail on regularly: Pearson 28-2, Rondar 505, Yankee 30, Blanchard Junior