I realize I'm in the tiny minority here, and don't expect to convince anyone to change their philosophy on the subject. That being said, if one assumes one has a finite number of cigars in one's collection, if you smoke your best cigar everyday, everyday you smoke a worse cigar than the day before. If you smoke your worst cigar every day, every day you smoke a better cigar than the day before.
I like having something to look forward to.
And what if that "forward" part never comes? To each his own, and I'm not trying to dissuade you from your practice. Your scenario is also assuming you'll never get any better cigars once you've smoked your "best", which I think is a bit of a pessimistic view.
Tomorrow is guaranteed to nobody. To me, the main things I consider when choosing a smoke is whether I'll have the focus and solitude to enjoy a great smoke or whether I'll be amongst a lot of people and the cigar will take a back seat. If I do, I'll grab one, no matter if it's expensive, rare, or whatever.
Cigars aren't for collecting. Internet pr0n, now that's for collecting.