I will be celebrating my 10th wedding anniversary next month, so I don't date cigars. Not that there's anything wrong with that.

All joking aside...I just read another informative review by Will. Jamie asked what year the cigar was, and Will promptly answered with the month and year of said cigar. I also recently purchased a couple great deals from Paddy when he put them up for sale. Each cigar he sent me had a sticker with a month and year on it. When I received the package it was the first thing I noticed. I thought about it a bit, and felt

1. This man must have A LOT of cigars.
2. When would be the best year and month to smoke this one? (Honestly, joking with myself at first, but really thinking about it shortly thereafter.)
3. What is the benefit to the time and effort? Is it really that important, and does it really make that much difference? What is the difference?
and
4. I wanna HERF with Paddy.

What I've come up with so far:
1. Yep, I bet he does.
2. I think there are so many variables, I don't know if there could possibly be a correct answer for this one.
3. I definitely believe there are major benefits, just not exactly sure what.
and
4. Yep, definitely wanna HERF with Paddy.

I guess the answer to the question I'm most curious about is #3. Any thoughts to help a newbie out?