Vintage vs. New, Risk vs. Reward

There are lots of respectable merchants for used vintage high end equipment.  Having developed my chops during the golden age of hi fi, the vintage has lots of appeal. The question is about the risk of making a rather large investment in what today “measures perfectly” but what tomorrow could quickly  end up a paper weight due to age.  This versus an investment in new which may bring with it, in addition to the probability of better reliability, but also the latest in technological advancement.  I recognize that “new” and “reliability” are much different (reduced) standards than years gone by (IMO/experience).

Appreciate your highs on this topic..