So one thing I'm doing is comparing value with apples to apples in mind. I've seen a Pearson 424 sloop. Nearly an identical layout. No teak decks, just toe rail, cockpit combing. It's been sailing the Caribbean for the last 4 years so its outfitted for cruising. Solar, generator, refrigeration, radar, davits, watermaker, autopilot. All the bells and whistles. Asking $56k.
The Bob Perry boat has a higher build quality than the Pearson, it's faster. Generally selling for a higher price point. Asking prices around $120k. Its a striking boat with the teak decks and it has a black hull. Seems like these two things make it harder to sell. Not outfitted for cruising at all. Doesn't even have refrigeration. Good things are its repowered but with a Volvo, rigging and electronics are 5 years old. Asking price is $65k. Seller is flexible on price since it will need to be outfitted. I've seen a 4 year old survey and it is positive overall.
Really the only downer about the Pearson is that I already own one, a 367. Feels like I'd be moving from a Toyota carolla up to a Camry. Lol
Sounds like a tough call, and I have no where near the necessary info to make an informed decision. Nor can tell which one really makes your heart sing, which to my mind IS an important factor when buying a boat.
IF the teak decks are in good shape ó and Iíd seriously NOT trust the seller on this one ó then the recent repowering and re-rigging is worth serious plusses. Not sure what boat you are looking at, but if it is significantly better designed and built vs the Pearson (which are known as good boats), then that also adds weight on that side of the column.
I discount most electronics; the basics are relatively cheap. Radar can be big, but where are you cruising? If the Caribbean, then my understanding is that radar is rarely needed. Refrigeration? Having just done the job itís not that expensive (boat buck or two) and not that hard to install in an existing ice box. Autopilot of some sort if essential, and that can be pricey. Not sure how the dark hull factors in. Iíve only ever owned light coloured ones.
Not sure how this all balances out in your calculations, but these are how I would balance what youíve said.