Every now and then I dream about going larger, until I start doing the math and decide that I don't need to take out that boat loan.
Although I've only been aboard for a year and a half, I have and do sometimes dream about going larger, and have repeatedly reached the same conclusion as you. Even though I've created a "what if
" budget that says, yeah, you could afford to take out a loan on that larger boat, I admittedly prefer to be debt free.
Now, if I had it to do over again? That is, picking the boat? Or rather, picking something as small as a 27 footer? That's a tough one. I think most expand to the space they live in. So, to my mind, bigger primarily equals more room for more stuff, which I really don't need. And sure, newer boats are pretty... eye candy wise. Otoh, my boat *feels* like my home. And of all the newer boats I've checked out, well... am sure they would too, eventually...
But for now, I love my funky little sailing home. Though, I am putting money aside in the event I stumble upon another boat that speaks to me the way this one did... while at the same time, I have decided to invest more seriously in fixing this rig up... already knowing it's money that won't be recovered, should I decide to trade up.