Maturity and longevity?

[Innkeeper]

You've gotten a lot of good advice here, like it or not. WOW points are well taken. Only a small number of wines should enter into your zone of concern. In your particular case since you are looking a '99 Chianti, the fact that you can't find one, might be that if any remain, they may not be saleable.

If the case of those wines that need age, ww is correct in stating that experience is the best guide. If you are young and trying a lot of different stuff, you need to rely on the experence of others. Over time, you will rely on your own experience. At age 66, I have a pretty good idea of when I will drink every bottle of wine that comes into the house. Even here, though, there are exceptions. A couple of years ago I was given two bottles that were way out the my normal league. Had to ask ww when to drink them, and he obliged. This is what I mean by experience of others.