Would you spend you money on modest brand new car or rather buy top notch vintage one?

Agree with hilde45. It depends on the situation and what you're looking for.

I would always buy new. Vintage can mean lots of problems and lots of money to repair.  Besides, vintage is thrown around way too easily here. 

For a car, I would buy the new one.  I have had old cars and there's always something going wrong/breaking on them.  Mechanical parts wearing out, rubber aging, etc.

For audio equipment, I would consider good used electronics, just being mindful of tube life and capacitor age.  Minimal mechnical wear and tear.

On that subject, I found this ad on USAM listed as a 10. This amp is between 28 and 32 years old depending on when it was manufactured. He says it's perfect, but I can clearly see a few small stains on the faceplate which is really not the point.

I messaged the guy and had a back and forth about the grading being improper for a used amp of this age and in the end, he dropped it to a 9. I think that the best that you can call an amp of that age is a 7. What do you guys think?

Threshold Sa 3.9e Stasis For Sale - US Audio Mart

I’ve already lived with the feature set in vintage. Cars have many more new ones every year. And besides tires there is less degradation from just aging except for seaside.