1. Find what you like in an AGED cigar by sampling lots of different aged cigars as singles or fivers - lots of readily available sources for that.
2. Once you find what you like in an aged cigar(s), buy quality boxes of the current vintage for long term storage.
3. Bite the bullet and pay the upcharge to buy a box of the aged cigar(s) (you determined you like) to smoke right now. Depending on how many cigars you smoke/week that will determine how many aged boxes you need to find.
4. Financially this may make the most sense.