I came to pipes late, but I applied a lesson that I learned via other expensive hobbies (musical instruments, firearms, etc.) - find the price point at which you get the best quality for the least money at a level that will let you enjoy the hobby instead of carping about your crappy equipment. A cheap musical instrument may save you some money up front, but if the fit/finish affects the sound or the ergonomics, it's going to be less fun to play. A cheap gun may be less accurate if there's too much slop in the fit, and may have a detrimental impact on training your hand/eye coordination. A cheap bicycle may get you where you want to go, but it's amazing just how much of a difference a few millimeters of adjustment can make in getting maximum mechanical advantage out of a relatively simple mechanism.
So too with a pipe. Witness the perceived difference between Chinese-manufactured cobs and a Missouri Meerschaum. Then look at the reputation certain "basket pipes" have vs. lower-end factory pipes vs. artisan pipes. Do the more expensive pipes "smoke better"? In some cases, definitely - in others, not enough to make several hundred $ worth of difference to most people. I started with about a $50 price point and did some research here, and eventually found that bumping that up to about $65 got me a better grade of pipe (still had to drill out the draft hole). My most expensive pipes have been between $100-150 so far, and that price point still has a lot of great value options for me personally (I don't have a Savinelli yet, for example, and just the one Stanwell).
I'm starting to look for my next PAD acquisition, and there are pipes from $90 to $250 (and a couple that break $300) that are the shape I'm leaning toward (somewhere along the continuum from a bent bulldog to a bent Dublin to a bent Acorn), so I just need to see what characteristics are most important to me, and whether breaking the $150 barrier is going to be worth it. I'm new enough to smoking that it's entirely possible that the smoking characteristics of a better grade of pipe would be lost on me, so going into the artisan/high-grade world would be a waste of their talent and my money, given the sorry state of my palate and technique currently. But in a couple of years, who knows? Maybe I'll make the same discovery that Fred Hanna did when he bought his first Castello... :D