I like Hiplains' post - pipe to pipe, you can assess certain fundamentals, and it's not that money makes them happen, but... at a certain price point, they are more likely to exist or be done correctly.
I think that price point is, roughly, 300 bucks. That's where pipes get really good, and separate themselves from the 150-200 dollar pipes.
Example?
Well, heck, I bought a 200 dollar "Punto Oro" Savinelli - this is their flagship pipe. And it's... okay. Not great, but okay. But gosh the heel gets hot. Why? A little experimentation, and ... great Scott... the drilling is so crooked that there is literally 1/32" of briar in the heel!
I would have been better putting that 200 bucks into a Castello, or a Ryan Alden. Even the Sasquatch cuts a better piece than that, I mean... jesus.
I see a vast difference in my "good" Petersons (140th anniversary, Sherlock Holmes, etc) than the "run of the mill" ones that are 100 bucks cheaper. And a vast difference between a bottom-grade Castello (at say, 300 bucks out of Italy) and a top grade Savinelli. I know many smokers who detect no difference at all. So be it. I sell pipes daily to people who do see and care about that difference.
As to "seeing quality"... I'm honestly not sure a new pipe smoker can do so. More likely you'll be dazzled by fancy bangles and shiny finishes, and things like the particular cut or particular bend of a stem will remain a little mysterious - and this isn't to offer insult, it's just the simple truth; it takes some study to learn these things.
I think most pipes at 150-200 bucks are about equivalent - you buy a Peterson, a Savinelli, a Stanwell.. whatever. But move up one notch on that totem pole, move to hand-made pipes made by people who care... and suddenly you've got a real winner. YMMV. I bought a Castello some.. 6 or 7 years back I guess, thinking "Good Lord this is expensive". I have a few more of them now, having proven themselves to be dead reliable as compared to other "big brand" pipes. Artisan-made pipes are another thing entirely, and there are lots of very good ones to be had, but again, 300 bucks is a sort of starting point for a very good pipe with all the details taken care of.