I have found CellarTracker to be an invaluable tool in my attempt to keep track of what wine I'm buying, who I'm buying it from and when to drink it to optimize enjoyment.

WIthout exaggeration, every wine-lover I have ever recommended it to has thanked me for providing them the link.  The only complaint has been along the line of "Ugh, I have 150 (or 300 or 500) bottles that I have to type into the software, why didn't you tell me sooner!?".

Fair point, but actually the software is user friendly and accommodates several different ways to build your personal cellar inventory.

Give it a try.