Very interesting thread! So many factors contribute to the smoking experience in addition to the engineering, aesthetics, artisan vs factory, status symbol, etc, etc.
Most of my collection consists of estates. Because of my fondness for Pre_Trans Barlings it could hardly be otherwise since they haven't been made since the early 1960's. But I also collect American artisan made pipes, and many of these are new.
Do my more expensive pipes smoke better than the less expensive pieces? For the most part, no. But many of the less expensive pipes, like the Pre-War Kaywoodies, were high grades in their day. They're just good values on the collector market. So for me, it's not how much I'm spending, as on what I'm spending. There are a lot of very fine pipes on the estate market, like Ehrlich, that are well made with quality materials, and which go for peanuts. It's about knowing something about pipes as much as it is about spending $$.
And ultimately it's about what makes for a memorable smoking experience for you.