A friend sent me this New York Times article by Eric Asimov (he's the nephew, BTW): To Study Wine, Buy and Drink. The article requires registration, but if you'd like to read it without signing on, you can always use Bugmenot. Or just read on, I'll give you the gist.
In Asimov's opinion, you get the most out of wine classes and books after you already have a working knowledge and a desire to get serious. He recommends that find a good wine shop, let them know that you'd like to learn, and have them help you pick out a mixed case in the around- $250 price range. Then, you take it home and drink it, preferably with food, paying attention to what you like and don't like. Take notes as you go along, recording how the wines interact and change with food. "The most important thing," he says, "is not how you describe the wine but whether you liked it or not, and whether you felt it enhanced what you ate or clashed with it."
When you're done, you take the notes back to the shop, discuss your experience, and ask them to put together a new case for you. Swirl, smell, swish and repeat.
To demonstrate, Asimov is actually employing this process himself and you can follow along on his blog, The Pour. You can find his case list (he actually ordered two cases from two separate shops for comparison) in the post The Dining Table Wine School.
While I don't agree with the statement that classes and books are only for the experienced, I do think this is a really fun and useful method and a great alternative if classes and books really do intimidate or disinterest you. If nothing else, you get to sample a lot of great wine and he's absolutely right in that you'll start to figure out what you like and don't. He's also right in that that's all many people want or need to know.
If you can't afford a case (and at the moment, I can't, otherwise I'd try and follow along with Asimov) there's nothing wrong with buying by the bottle. The most important thing to understand is where to buy it and what a good wine shop is. As I heard Diana Hammond, the Wine Goddess of the Chopping Block, repeat over and over: the grocery store is not a good wine shop, nor is Whole Foods or the World Market. While the employees may have some knowledge of wine, they usually don't know enough to make a real recommendation. These places are fine if you already have some idea of what you want, but a good wine shop will have employees that really know wine and can make knowledgeable recommendations based on the information you give them.
The second most important thing to know: if you want a wine shop to give you a recommendation, you need to be able to give them a starting point, at the very least a price range. Choosing whether you want a red or a white is helpful, too. You also need to be open minded. If you go in and ask for a really good wine for under $10, expect to be given a recommendation for a wine that you're not familiar with. The most familiar wines (i.e. Cabernet and Chardonnay) are often the most expensive precisely because they're the most familiar. Be willing to try something new, and no nose-wrinkling! If you don't like the wine, feel free to return and say so, but at least try it.
If you live in the Chicago area, there are a ton of good wine shops. Diana always recommended the Wine Discount Center and I've always had a good experience there. There is also an extensive (and recent) list available on the Chicago Sun Times website: The Best in Bargain Wine.
If you are a class and book person (as I am) I highly recommend Diana's wine classes as the Chopping Block. She is extremely knowledgeable, very accessible and not at all snobby. She also offers a Cheap n' Good Wine List on her site. As for books, Eric Asimov does cover his recommended reading list in the post School is in Session, but for a light and entertaining introduction to wine, I highly recommend Drinkology Wine: A Guide to the Grape by James Waller. The information is there, but it's also an easy read.
So drink up and stimulate those brains cells! Apparently, a recent study found that Light to Moderate Drinkers Show Greater Cognitive Ability. True? Who knows, but it sounds good! Cheers!