I don't look at value in a boat as strictly monetary, though it is a part of it.
We find we have great value in our boat as a vacation home. As such, a trawler suits our use perfectly, as it has many of the amenities a waterfront condo would have, at a fraction of the cost. Plus, if we get tired of the view, we can move it.
As for your determination, I agree with #1 entirely. 90% of our use is daytrips or being a dock queen in our own slip. As such, comfort at the dock is important, so we have a wide cabin, a substantial cockpit, and since we're in Seattle for longer than just the summer, covered side decks. :-)
#2 & #3 sound like you are looking at the boat as an investment. It's difficult, IMO, to consider a boat an investment of any quality, and it would not be part of my criteria. I would just look for a boat you like that can be purchased at or just below current market rate.
#4 Is also not part of my criteria, in that I have never gone back to the original manufacturer for support on my vessels. That said, I have owned very common brands on purpose -- It's generally easy to find a part for a Catalina or a Bayliner. If it's a custom build, I would look very carefully at the systems installed and make sure they are common and that it's easy to find replacement parts.
I would add other criteria to the list that we consider "value":
#A: Fuel Economy. I'm not talking about the difference between 1.2GPH and 2.1GPH... I'm talking about the $600 fuel bill for the WEEKEND on my 28' Bayliner, vs the $300 fuel bill for my current trawler for the YEAR. It's changed how we look at going on boat trips.
#B: Creature Comforts. Well planned layout in the length we were looking for. A good heater. An autopilot. Radar. Easy access to machinery. These were the things I saw in our current boat that made the decision to switch easy.
#C: Market price. We purchased our boat for way below market, as it was a friend of a friend, and they didn't want to go through the process of listing it and what not. It was a win-win for both of us in the end. If I can find a similar deal, I'd do it again -- the trick is not to be on a timeframe at all. If the boat shows up for us tomorrow or in 4 years, we hope to be ready to jump at the opportunity.
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