I learned years ago that cost doesn't not necessarily mean quality or satisfaction.
So true Warren.
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Nate, what you seem to be looking for are "the most highly regarded pipe makers", and there are many many darlings to the "ultra high end" collectors - but that doesn't mean the pipes actually smoke any better than anything else, what makes them "the best" is the esteem and regard that whatever individual maker has established, where deep-pocket people are willing to spend extraordinary sums of money based on the makers place in the pantheon.
In "real pipe world", any perception of "the best" goes right out the window, it's quite possible that a $5 basket pipe can smoke better than a $1,500 masterpiece - that's a well-known fact.
If your goal is to establish a collection based upon and consisting of the classic pantheon of acknowledged master artisan pipemakers, then you have a very daunting task ahead of you because not only is that list extremely expensive to acquire, but the competition is very fierce --- sometimes a "masterpiece" with a super high price tag will sit on a sellers shelf for a long time, but in many cases they're snatched up quicklike, and most of the seriously desirable examples get exchanged between well-established advanced collectors and never see the light of day anyways.
The search may be exhausting, for example, finding a really nice Jorn Micke is a difficult task.
The best strategy, or what I would do if I were in your shoes, would be to narrow my focus to a specific aesthetic style or shape, or certain country, it'd make the process a bit simpler.
It is a noble quest, but Galahad never actually found The Grail, and most pipe collectors don't either - in most cases we are all chasing windmills, tilting a valiant fight but often failing to meet perceived expectations, at least in regard to the ever elusive "perfect magic pipe".
I remember reading a Rick Newcombe passage where he was asking a well-respected collector about how his Bo Nordh pipes actually smoked, and the honest collector said "...about the same as my old Stanwells."
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