[bmajvi]

Most of my experience in “moving up” in size has been on sailboats (now have a 40 footer), and I’d offer that there’s probably no easy answer – it really depends on your idea of how/when/where you’re going to use the boat. Bigger boats generally seem to get used less than small boats, I think because it’s usually a bit more of a production to get the bigger ones ready to go + more to clean up afterwards = less spontaneous “Let’s go out for a few hours.” Single handing a larger boat can be a PITA around the dock (& trailering).

Boats grow geometrically, not just in length, so trailers, dockage, haulouts, paint, wax, canvas, hardware, cordage, ground tackle, fuel burn, etc., are all bigger/more expensive, so the up front and ongoing dollar commitment grows fast. All that said, if you have the time, money, desire, and it fits your expected use profile, a larger (quality) boat will probably be a lot more comfortable and safer when the weather turns cruddy.

If after thinking it through it feels right, I’d say go for it…you should be able to get a good/great deal in this market, if you’re careful you may be able to feed the “big boat bug” with limited downside $ potential. Good luck!