When I first started smoking pipes, about 4 years ago, I had come into a bit of money and spent almost $10,000 on pipes, both new and used. I found that there weren't a lot of compelling reasons to spend a lot of money, since I didn't see a correlation between expense and smoking pleasure or taste. I do have a couple of commissioned pipes from Tyler Lane and Andrew Staples that I bought because I really liked the looks. These pipes do smoke very well. I also have a couple of good meerschaum pipes, which again I bought for the looks (one of them is a carving of J.S. Bach, my favorite Baroque composer). I have a few Dunhills, Savinellis, and J.M. Boswell (great value for a hand carved briar), but avoided ebay in favor of Marty Pulvers for used pipes. That's just me, some folks have had good luck on the auction sites, but Marty has never done me wrong and his prices are very good for the merchandise.
I know I've veered off topic and expect the topic police to find me. Sorry for the long winded useless information.