I find that, when comparing Vampire: The Dark Ages (VDA) to it's modern counterpart, Vampire: The Masquerade (VM), VDA seems to always come out on top.
Unlike VM, VDA allows the players to exist in a world much more open and less ruled by the extremely irritating, corrupt web of the Camarilla and Sabbat. In fact, those two sects don't even exist: every vampire becomes an entity unto itself, under complex rule by no one. This allows for great freedom of expression in gameplay--expression that is all too stifled in VM.
Also, the book itself has MUCH more in the way of setting. The VM book, Revised Edition, seems extremely vague in the descriptions of the 13 clans. I could not help but be enraptured by the mysterious Dark Ages Assamites: in the modern day, they are static and more or less boring (at least based upon the meager descriptions found in the main core book). In the Dark Ages, they burn with life and passion. This is only one example--virtually every clan falls into this category.
The Dark Ages' own inherent mysteriousness and superstition allows for much more varied gameplay as well--the science of the modern day detracts much from the vague--but interesting--origin of vampiric power. That strange sense of wonder is present in the Dark Ages, but in the modern day VM it is simply in the way. One feels like vampires should have been scientifically explained by now, in our day.
Anyway, in short, the Dark Ages are a much better setting to be a vampire. You have more power, more mystery, more varied gameplay, and above all: freedom. Also, that whole blasted "punk" thing is done away with--when I think of vampires, I think very little of rebel hoodlums on a street corner. ;)