When I bought my last boat in 2002 (Bavaria 36) I thought that it would be my last sailboat and could well have been. I sold it in 2009 because I had the money for a better boat and because the boat was approaching the time where I would have to spend some serious money in maintenance: New sails, new standing rigging, new running rigging, new epoxy barrier, new batteries, new spraywood, new bimini and in not much time, new electronic and a overall on the engine.
All that money would be wasted unless I stayed with a boat otherwise it would add little value to the boat (I learned that the hard way).
The boat still sails exactly as I have sold it, with the same sails and all, but the Italian I have sold it to don't use it like I used to do, I mean with long range cruising.
With proper maintenance a boat like that can be around for more than 30 years and that means that would have lasted all my life.
I preferred not to waste any money on the Bavaria maintenance and add that money to the value of the used boat to buy a new boat that will be maintenance free for the first 10 years or so.
The new boat will not be much bigger (2ft bigger), but more modern, faster more seaworthy and nicer and it certainly will outlast me
A last comment regarding cultural differences: I have noticed that many Americans talk about new boats as if they should last 50 years or more, and see defects in building techniques and details that instead of lasting 50 years will only last 30 or 25.
Nothing wrong with that but the funny thing is that while on Europe we tend to look at the boats as timed limited objects (maybe with the exception of the British), like cars, we tend to look at houses as hereditary objects, I mean, many houses are own by the same families for centuries and they pass from father to children. As result the traditional European house is built to outlast its owner and the generations to come while the American traditional house (I am talking about single houses) is built in a much less solid way and has a limited duration.
Of course it makes some sense to build a house to a limited duration, like boats, it will be a lot less expensive, but if you try that here nobody will want it even if the house will clearly outlive the owners time frame. I guess that the same happens in America regarding boats