I dunno sarge, my favorite Havanas are from '04, it's just a matter of personal preference.

I have found that quite a few Havanas from the 1998 - 2000 years have a higher chance of quality problems, rolled too tightly and are therefore plugged.

Unlike wine where grapes from different years taste differently, cigars age as a function of time so if you like the taste of aged cigars, the older the better but again certain people tend to avoid certain years based on quality problems they have either heard about of experienced first hand.

I've never heard that tobacco from a certain year tastes better than from other years (like wine)