If you are really serious about getting a lot of wine, I would suggest taking a trip to Sonoma/Napa. Spend a week going to various wineries, doing taste tests, and experiencing the huge range in variety and quality available. Many of the wines sold there are not easily acquired in the DC area, and nothing beats being able to taste before buying.

Find some that you like, and bring/ship them back. At wineries that have something you really like, you can buy futures (think a pre-order for a upcoming year vintage) in wines that you will probably never see on the east coast.
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