Re: Smallest boat you can live with
We are strong believers in the concept: cruise in the smallest boat you can stand to live on.
We owned 5 boats over 30+ years starting with a 22 ft boat, maxing out at 52 ft, and ending up at 38 ft. The 52 had 3 air conditioners, a generator, power winches, power furling, 15 electric pumps, water maker, 2 heads with separate showers, etc. I believe there were never 7 consecutive days when everything worked. To replace a sail, I needed assistance just to move a sail bag. When everything worked, I single handed it. When things broke, not so much.
The 38 has simple systems, we had it built so that everything is accessible. There's nothing I cannot fix, but its so simple hardly anything breaks.
Our mission is coastal cruising and day sailing with an occasional passage for a couple. Admittedly if we were full time cruisers, I'd go bigger, but I'd try to live in the low 40's, trading up some complexity for more comfort.
On a small boat, you'll see the same sunset, you'll feel the wind more (less like driving a truck), you'll fit in smaller anchorages and marina's, you'll spend more time sailing/less time fixing stuff, you'll sail to moorings more often, and you'll spend less money. Operating costs are exponential increasing with length.
The ratio of fun / dollars is highest on the smallest boat you can stand - IMHO. I don't think we ever had more fun on any boat than we did on the first one, a little Pearson 22 with worn out sails, a compass and depth sounder for navigation, and a little outboard to push it when the wind died.