Wow! Lot's of advice, and virtually all of it's good advice. I'll try to be specific...
1) On Churchwardens: I've owned several churchwardens. I think it's an Old Wive's tale that they smoke "cooler," but they also don't smoke hotter. If you like the style, try one -- although I would add that, due to the size, I don't smoke them much. I like to read, type, and have my hands free while smoking.
2) Buy Savenelli. I don't believe there is a better pipe maker in the price range. I've got some expensive briars, but most of the pipes I smoke are Savs or house pipes from a local B&M.
3) A corn cob might be the best place to start if you've never smoked before. Most guys who try pipe smoking don't stick with it, for a number of reasons (tongue bite probably being the leading culprit). A corn cob from Missouri Meerschaum would be cheap, plus cobs are very forgiving.
4) In general, if you're buying briar, get the best you can afford. That being said, don't be afraid of "house pipes" or Dr. Grabows. I own several Grabows that I'm seriously attached to because they're really good smokers. On the flipside, when you buy a Grabow it's kind of a crapshoot -- I've ended up tossing or trading a few because they weren't very good.