So ............... how old is you boat, how long have you had it, and how many owners have been "maintaining" it? What do you think of the care the past owners did to the boat?
NWD is 45 this year. I believe she has had at three owners prior to me. One was, likely the original, owned a prominent roofing company in the Puget Sound region. His las name was Crowe, and he originally named her Old Crowe. I do not know who the second owner was, but her name had been changed to Rejoice by the early 2000's. The last owner had her from 2008 until we bought her in 2018. She has four or five stick on awards from the Seattle Yacht club from the late 90's and early 00's above the stairs down to the aft cabin, so back then she was likely well cared for. The last owner put a lot of initial work in on her, then several years before putting her up for sale he had a stroke and wasn't able to care for the boat much. He had updated the electronics, added a nice RIB with a Yamaha outboard, and a really nice Seawise davit system. From the condition of the engine room and some of the other things we found on the boat, he wasn't necessarily handy mechanically/electrically. He told me he resealed the windows, and that they were never gonna leak. He used 5200 on them. He didn't use some things, and they didn't work, of course. Somehow, he got it in his head he could put a bronze impeller in the raw water pump so it would "never need to be replaced", but it wouldn't prime or pump water (I'm guessing that was post-stroke.) There is documentation of him hiring out work, IE shaft work, engine/transmission work, inverter install, etc and most of that seems to have been on par.
At some point, the entire boat has been painted, and its now faded/cracking and needs to be refinished. Not sure who painted her when. She could have used new paint the day we bought her, but I haven't had the time to do it myself, or the $ to pay someone to.
I think people have changed the oil in the engines and transmissions; they purr along just fine. I put a lot of initial work into her to fix things that came up on survey or that concerned me. Redid the sanitation plumbing, repaired the existing tank, added a second one for the forward he, etc. babied the engine room, moved batteries to better locations in proper boxes, added waterlifts to the engine exhaust, etc.
In short, I think each owner has likely taken good care of her at some point, but then "health forces sale" likely happened at least to the last two owners. I was supplied with the last owner's survey he had done when he bought the boat, and it was obvious it was unused and needed a little TLC. We still found unresolved issues form that survey on ours!
All that said, we were able to pick up the boat in Squiem WA, enjoy a 3 day weekend on her before hauling her in Anacortes for some of the work we wanted to do. Except for the regular radiator hose that had been installed on the generator exhaust elbow. And the batteries could not hold a charge. But that's another story.
Not knowing anything about the original or second owners like you do, I have no idea how the boat was taken care of. It seems mechanically well overall, cosmetically its been in steady decline with some times of renewed attention.
I wish some of the previous owners had done more work that would make it easier to maintain her - like fixing the windows right, etc. But, if they had kept it up a lot better, I wouldn't have been able to afford her, so what do I say?!