[massphatness]

There's no right answer to this question, and like Michael said, it's a matter of personal preference. Many cigars, like many wines, are great fresh. Others mature over time and undergo multiple flavor changes as they age. Personally, I prefer the more nuanced flavor of a cigar that's sat for 10-15+ years. However, that doesn't stop me from smoking & enjoying recent production sticks.

One rule of thumb I do try to follow: when a new shipment of cigars arrives at my house, I try to let them sit for a couple months or more to give them time to settle down from their journey, all the jostling around and the various environmental changes they've been subjected to in transit (including the trip to the freezer that every box makes before I'll put it in my humidor: no beetles for this guy).

Experiment! Find what you like then experiment some more.

Good luck on the journey