Almost 3 years ago I bought a 1986 Mercedes. One of the nice things of a classic car (at least, here in the Netherlands) is that you can get an insurance based on an official appraisal of its value. Which means that if I total the car, that's the amount I get.
Now such an appraisal is valid for 3 years, so I had to renew it yesterday. Interestingly, the value had increased with € 1000!
Don't think that would have happened if I had bought a regular second hand car at the time.
As to maintenance, I've had, besides the regular oil change etc, 2 shock absorbers, two new tires, and a new airco pump. Not that much.
So far, I'm quite pleased.