This is an interesting question that has a lot of perceptive answers. And perception is everything.
We had a 1984 Endeavour 40' CC for about 7 years. We took care of it, but did not perform any major refit other than having the bottom skimmed and redone with a new layer of fiberglass, new barrier coat, new bottom paint after finding the very thin bottom after purchase (37 layers of paint hid the 10's of thousands of tiny bubbles). We were new to the game then. We babied the engine, it had an unknown number of engine hours but it purred otherwise. Over the years of ownership we sailed and sailed, up and down, around the Bay. During those years we realized that to be the boat we wanted it to be the engine would need a rebuild, no a replacement, too late for a rebuild. She needs de-masting and new rigging. The electrical system was an 80's and beyond hodge-podge with many problems from previous owners. We both work full time jobs that do not involve leaving us time during the week to go work on a boat. The weekends were dedicated to me making sure my daughter (from another) got as best a childhood possible, or sailing. I'm not a mechanic, or HVAC tech, or an electrician, but I wanted to play one on TV so I started learning as much as I could. Meanwhile a real diesel mechanic kept the motor going as things started breaking on the engine and we did the maintenance in regards to filters, oil changes, bleeding the fuel lines, etc.
Fast forward a bit to more recent and then we realized that for it to be what we wanted, it needed to be hauled out and worked on for a season to to a major refit. Or... we sell and buy another boat that we thought had things we want, or more easily install the things we want with a better canvas so to speak. The purchase of the current vessel 20 years newer provided that option. The 2004 vessel has newer design concepts, sails better, faster, and we could get that shiny new electronics array and install it ourselves after purchase. Decent sails, slightly torn genoa, well we can get a new one of those made and a new main in a few years too. We work hard and pool our resources to do those things and like many have said, couldn't care less about our vehicles other than that they are pretty dependable because of those jobs.
One day we hope to cross paths with some of the awesome people who I see posting on the forums, and avoid the salty ones of course.