Titanic, I think the smartest collectors are the ones who *start* with higher end pipes. If I could start over, instead of buying four $50 pipes, I'd slow down and buy one $200 pipe.
But it really all depends on what kind of money you want to spend.
I've bought a lot of them, from spending $10 on no name pipes, up to spending $300 on certain Italian pipes. Of course, you can spend more than that, but I havent got there yet
My advice is still to decide what price you want to spend on your pipes, and then find the best deals on that range of pipes.
My experience is that a certain name on a pipe is almost a promise of a certain level of quality. Sure, you might find the odd GBD or Stanwell that doesn't smoke well, or the shape just doesn't suit you.
The good thing is, if you buy at good prices, you can typically relist them and get your money back.
For me, I've settled on Italian pipes.
Ser Jacopo, Mastro de Paja, Don Carlos, Rinaldo, Brebbia and Armellini are the briars I smoke and enjoy the most.
I have also kept a number of individual pipes I collected over the years that just fit me. I have one or two Custombilt, Stanwell, GBD, Savinelli, Nording, Jarl, Neerup, Amphora, Wally Frank, Corncobs, etc.
They're all great smokers, but I've resold twice as many as I've kept.
Then again, if I had concentrated on higher end pipes the whole time, I'd have twice as many of those, and probably not many cheaper pipes.