With all due respect this question shows someone who is clueless about boats and what they want and what they need.
What any member on SN wants, needs, and would or have looked for in a new to them boat is completely irrelevant to YOU/
Of course you don't know what you don't know. Everyone faces this problem. But each person is in a different place in life.
It's self evident that an older boat, even well maintained is going to have more expense in terms of service, maintenance and needed refits/upgrades... especially if it has been normally used. Unlikely to find a used boat all tricked out to what you want and need that is in bristol condition and rarely used
You definitely need to figure out your financial situation to drive your choices, purchase and refits/upgrades. No one can give you much advice on this. Some are conservative and risk aversion... others the reverse.
Look at the reputation and various owner's comments about the boat you are interested. Take everything with a grain of salt.
And then you need skills to tackle the work on your boat... or pay for someone else to do it and hopefully understand what they are doing and charging and so on.
If you see a boat that you can afford going it, get a surveyor and have any closing subject to surveyor's findings. Tell the surveyor what sort of sailing you intend to do.
Go back and do your homework.
With no respect, you know where you can stick your advice right?
You wouldn't make a pimple on my a--!
It so figures, there's always some tight a-- Troll like you on every forum without fail that just loves to talk down to people and start trouble.
Here's a suggestion, don't like the subject? don't reply!
Just because you have a stick up your a-- and decide you don't like a subject at hand doesn't make the person asking incompetent for doing so, nor does it give you the right to belittle anyone when you don't know what the hell you are talking about, the problem here is YOU
and your sanctimonious, self-righteous ego.
Its a simple inquiry question to what others have already gone through but obviously, you don't have the intelligence to understand that.
I had no idea that this forum was yours and yours alone, in that no one is allowed to ask something (first to be approved by you), that might anger a smug bastard like yourself and then you attack them for doing so.
What a tool you must be in person.
Get over yourself...