Re: Bit by bigger boat bug - strip the old boat or refit new one?
We've been there and decided that except for a few personal and family heirlooms (ship's clock, bell from my dad's boats, etc) , we sold the old boat as is. The upgrades were what make her what she was and she sold quickly.
I understand your quandry. In my case we boat a larger version of the same boat (moved from Sabre 28 to 38), so all the stuff that I did to the old boat I had to buy again and do over. It was discouraging for a few weeks but after a couple of seasons, things were right.
We tend toward a minimalist approach, tending to remove extraneous gear and simplifying the boat. I removed a lot of stuff including lazy jacks, a hot water heater, dead engine-driven reefer, LORAN, ancient GPS, old VHF, etc.
Sabre 38 "Victoria"