I wonder how many others have this issue...
There's a natural desire to have a boat two feet longer. In that case, for us, a 36 footer. Maybe a pretty, cream-colored Rival 36 from the radically modern late 1980s...
However, we have a tendency to buy older, heavier sea-worthy boats. We like newer and lighter and longer boats, but either a) they seem expensive or b) they seem flimsy. And c) in our price range, they are coastal cruisers.
So, heck, we're coastal cruisers right now, but we've been out in 45 knots, and the channel can be more than a bit rough, and boats need to be a bit beefier here (or the sailors more skilled with race boats, which seem to have stainless that bends quite willingly in strong winds on the Fastnet). Yet, there are many happy Jeanneau and Beneteau owners here as well.
So, we have a heavy but comfy 34 footer, all paid off, and there's still the thought of "wouldn't 40 feet of something be nice." Is it essential? No. Would it be more comfy? Yes. Would a loan be involved? Yes. And what about the kid's college funds? Ugh.
There's a lot to be said about having a boat paid off. A smaller boat is more affordable to keep in good nick, and buy new winches for, and do nice upgrades on without breaking the bank. And, plenty of our breed (Rival 34s) have done Atlantic circuits, and raced to the Azores, etc. It's just different mindset from having a Malo or HR or 44 foot cruiser/racer.
So, the year-to-year conundrum-- invest in the owned boat, save for a big boat, master the small boat, plan for a bigger boat, or go small/go now, or go once the kids are off the college (when a smaller boat becomes larger, and really one shouldn't have a boat two big for two empty nesters to handle anyway).
Sure, there's no one answer, and we're lucky to own and sail anything at all. I just wish the question would be less distracting.
Anyway, off to work on the 34 footer tomorrow, a little piece of home for a family of renters...