My first pipe was a Dr. Grabow bent billiard, can't remember which model, that I bought off of the board at the Rexall drugstore along with a pouch of Borkum Riff Black Cavandish. I selected that pipe because I could afford it and I thought it looked cool. I then proceeded to make all the mistakes novice pipesmokers make while learning the art.
45 years later, I still have that old Grabow. It's much like me, scratched, scarred and a bit scorched about the edges. It still smokes great.
I own more pipes now, of all kinds, and several are very nice. But if I could only grab a pipe in each hand before evacuating a building it would be my Grabow and my second pipe, a Bachus Head meerschaum, that a friend gave me the next year.
My advice to the new pipesmoker has always been to decide what price point is comfortably within your budget and then go buy a pipe that you think looks cool and feels good in your hand. There are many different tobacco samplers available these days, pick one that sounds most interesting to you along with a tamper, pipe cleaners and your preferred flammenwefer, and get started.
It truly is a journey.
You'll figure out the rest along the way.
Cheers!