Go with a couple or three Missouri Meerschaum cobs.They're all terrific pipes. For my tastes, I like the Mark Twain, the Diplomat, the General and the Freehand. If I were to get only two, then the General and the Freehand. (Get a tamper/pipe tool and a couple of packs of pipe cleaners while you're at it.
Spend your money on good tobaccos to start. Some will advise going with mild aromatics but Greg Pease (You will get to know the name) suggests a mild to full flavored blend.
I recommend n that you get a good sampling of well reviewed blends of different types: a good Virginia (Samuel Gawith Full Virgina, a Virginia/Periqu,(Escudo) a Virginia Burley, (Magnum Opus), an English blend (maybe Squadron Leader) and an aromatic (Lane IQ).
Alternatively, you could get the GL Pease Sampler from Pipes and Cigars. It includes 6 really good blends.
This will get you going for a few weeks to a few months. Afterwards, you'll begin to have some idea of the types of tobaccos you like. You can then get more cobs or start your briar collection. I strongly recommend that you get name brand pipe and budget $80 to $100 for your first briar if new.You want go wrong picking Savinellis or Stanwells.
Alternatively, you can get an estate pipe from Smokingpipes.com, Briarblues.com or http://mkelaw-pipes.com/ for as little as $50 to $60. You can trust these guys and you will get a great smoker.
I would avoid the bargain briar pipes especially the grab bag offered by P&C. If I could do all over again, I would buy fewer pipes but higher quality, and spend the money the money saved on good tobaccos.
BTW, these are just blends and brands I happen to like and there are other great alternatives. The guys here at PipesMagazine will take care of you.
Pax