Re: Pitfalls of trading up?
Never been in the 'always buy new' set.. but until the last change did go up in size. The 'downsize' attempt was much more difficult. Going from 28 to 40 feet 20 years ago was awesome.. awe-inspiring maybe even... Trying to go back to 30 feet after that proved impossible, we ended up (happy) with 35 feet.
Depending on the moorage market situation moving up can be a real challenge on that front.
What I REALLY RECOMMEND AGAINST is buying one before selling the first. Owning two boats is a pain, costly and invariably the one for sale falls into neglect and disuse and therefore 'shows' poorly. BTDT, and don't plan to do it again. Occasionally a 'smokin' deal' shows up to tempt you, though,......
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)