Brian, B-Dub, I am a pipe smoker. You may find something you like among the recommendations of others, but like bourbon, you just have to get around to tasting them all and making up your own mind about what you like.I am just starting to get into pipes, and was wondering if any of you were pipe & bourbon people. If so, what are some of your favorite pairs of the two?
http://pipes.org/ is one of the best online resources to educate yourself about pipes. You can sign up for the Pipes Digest e-periodical, and join the discussion groups. I also posted a link recently to tobaccoreviews.com, which is a great resource on tobacco tasting.
If you're not sure whether you'll like it, start with a corn cob. Don't laugh: all pipe smokers know that cobs smoke very well. They won't last a lifetime, but they smoke cool and dry. And they're cheap, so no great investment lost if you don't stick with it.
But stick with it. I can't emphasize this enough: it takes time to learn how to smoke a pipe properly. You will get your tongue bit, when you're new. You will go through matches til you learn how to keep it lit. You have to learn how to load it, and how to light it, and how to control the rate of combustion through gentle air flow... it takes time and practice. But it is an exquisite pleasure once it becomes second nature.
Go to your local pipe/cigar shop; if the pipe smoker isn't working, ask what his schedule is, and go talk to him. Pipe smokers are always glad to educate a novice. Sniff those jars. There is no ultimate blend, just like there is no ultimate bourbon; the pleasure is in discovering the myriad of tastes to be had. Smoke some straight burley, to discover what it tastes like. Smoke a straight virginia, too. Smoke a straight cavendish. Find out what the different tobaccos taste like, then see what they add to a blend.