I have never purchased a pipe for over $1K, but I have come close, and I have a couple that might sell for that price now. When I collected, I would purchase one-of-a-kind pipes, always from individual carvers or boutique houses. They were, and are, very beautiful to me, and there is a story behind each one of them.
Having known a few carvers, I can tell you the job appears to be a labor of love; these people spend alot of time and money equipping their shops, buying raw materials, etc...and they lose every time they start carving and later find a fissure or defect in the wood. Considering the time/cost of material etc....very few of these folks are going out and buying fancy cars with their proceeds. Some of them don't make it....they try and try but they can't make enough $$ to stay in business.
I'm a thrifty Yankee now, and the only time I acquire a new / special pipe is a very rare occasion, and I acquire it in trade. Now....making a carver rich because they have a hard job is not "our job", if you will, but I can understand why a carver might feel that they produced a masterpiece, and they may have put many many hours into it, maybe many many days of hours. Is their "art" worth our money? Sure, for those who have the money and interest in it. As others have said, it's worth it to someone, and by the number of pipes I see on SP and elsewhere for over $1K, there are collectors buying them. Thank goodness for that, because it gives carvers a light at the end of the tunnel.