My wife and I have a great thing going at MacArthur Beverages in DC. Once a month we give them roughly $200 and our guy there picks us a dozen bottles of red. We note what we like and don't like, and take that information to him the following month, and repeat the process.
After the first two months of doing this, he had us nailed. And the store loves it because we are a steady diet of feedback (and cash flow).
This is how I figure it: we have a rotating wine collection of several thousand bottles a few blocks from our home, a personal wine manager who is continuously updating his knowledge of our preferences, and access to a dozen bottles a month, all for $200 a month.