I was browsing for pipes the other week when I came across a recommendation for Jan Pietenpauw.
His description of pipe value seems true enough:
Only recently did I start carving "proper" pipes and thought that I might offer some for sale. My pipes are reasonably priced (some are downright cheap) only because I am not as famous yet as some of the great names in pipe lore.
He actually changed the quote on his website recently but Pipedia still has the old one that I think better explains the industry, though he may have decided recently that his motivation for not asking more is different than it once was.
Another example I can think of is Randy Wiley, surely he's been in the industry long enough to command a higher price. I would bet the only difference between his pipes and a "high grade" would be that he isn't a second generation maker from Italy.
You can probably say the same for a Savinelli, the price is mostly just representative of availability. If Ashton made 100,000 pipes every year they might cost a little less too.
The bottom line as I see it is simply supply and demand. Someone doing exceptional work will eventually have more customers than time, then the customers bid each other up, and the average price goes well beyond the practical value of the product. High prices are probably just an indicator of supply.
I have a small collection of British pipes, and I purchased them knowing full well that a good part of that price was the "Made In England" stamp. I've come to accept that the only part of those pipes I expect to be functionally superior to a factory pipe is the Briar selection and treatment (and even oil curing is largely for aesthetic purposes).
In fact once I get the excessive bowl coating out of the draft hole my $40 Rossi will probably smoke better than my $280 Ashton.
I didn't run out and buy an Ashton the moment I read about them though, it took a few months between starting and actually making a purchase. I have two of those now (the second on a deep discount), and hopefully they're also my last.