The Admiral and I bought the smallest boat in which I could
comfortably stretch out in at least two of the berths, which happened to be a 30' boat, based on the premise that what we were largely going to do was cruise. Well, here we are, two seasons later, having done no more than having over-nighted on her a couple times with the boat in her slip

. We day-sail and (club) race. Knowing what we know now, would be choose differently? Perhaps. Perhaps not. That 30' really isn't all that difficult for us to double-hand, and we
still plan to cruise... eventually.
Btw: In our sail club (note I wrote
sail club, not
yacht club), we're one of the "smaller" boats

.
Btw2: Both of us had sailing/crewing experience before buying Abracadabra, so we more-or-less knew what to expect.
Jim