I do have to agree with going briar first. I would suggest you get a relatively decent pipe from the start. It's a one time investment, if for whatever reason you don't like it, you can always sell it for what you got it for on Ebay. I would agree with the mention of Peterson system pipes. My first pipe that I bought was a 303 System. However, the first pipe I ever smoked was a no-name pipe that my buddy had snuck away from his dad. The key is to find something that:
A.) appeals to you aesthetically,
B.) fits your price range,
C.) appears to be within your price range and
D.) has a proper fit for you
What I mean by "fit" is that you want to feel comfortable holding your pipe. Given that the size of the bowl varies per pipe, you could end up holding it either in your mouth, your hand, or your pocket for hours! It may as well be something that you don't mind and can be quickly accustomed to. Do not under any circumstances feel hesitant to ask your local tobacconist what he thinks. These guys typically are not in a market to rip you off. The Tobacconist still caries on an old-school tradition of remembering his customers names, preferences, and BS stories. Many will be more than willing to help you to a pipe you will enjoy.
As for tobacco, BE WARNED!! Although the cherry and vanilla stuff is nice for a little while (not to mention it appeases the significant other) keep in mind that eventually you will be VERY VERY tired of it if you smoke nothing but. I would suggest you start on some non-aromatics or at least non-flavored tobaccos. I think you may really enjoy a Cavendish blend. Cavendish is a mild in flavor, yet very pleasant smelling and tasting tobacco that always has a caramel-vanilla taste to me. It tastes this way fairly naturally. Your best bet is to go to your tobacconist and sample a little of each.
ALSO EXTREMELY IMPORTANT!!!!!
If you buy a pipe that is not already broken in, PLEASE take caution in breaking it in. To break a pipe in is to coat the inside with its first few layers of carbon. This is done by smoking the pipe starting at a half bowl and moving up and need be done to prevent the pipe from cracking. If this sounds intimidating (it really isn't that big of a deal once it's explained) I would look into a previously used pipe. They are already broken in, and you can get nice pipes for very low prices. Ebay would be a good source for this as I have personally bought some of my very best pipes there used.
Best of luck, I hope this was of some use!