Most expensive pipe was my Stanwell Nanna Iversson, that I paid around $250 for. It is a very good pipe that I will keep for a very long time. In Chicago this year, I decided to up my collection with some higher priced pipes and I believe I learned something. I purchased a Ryan Alden pipe that is fantastic, the most comfortable bit and button of any pipe I own by far, and it is a great smoking pipe, right at the top of my pipes. However I have 2 other pipes that smoke just as well that are factory pipes, a Brigham Chinook 426 and a Peterson Ashford 03. The Peterson offered the very best smoke out of a first bowl of a new pipe that I have ever had. The Alden pipe was incredibly reasonably priced and should retail for double what I paid for it. Aesthetically it is the best looking pipe I own as well, people are constantly commenting on it. However it does not smoke twice as good as my Pete or Brigham, not a knock at all on Ryan's pipe, just that there are very well made factory pipes out there as well. So it's a tie for my best pipe between the Alden, Peterson and Brigham.
I also picked up a barely smoked Dunhill Cumberland Group 2 billiard at about a third of the retail price, and while its a gorgeous pipe (almost as pretty as the Alden) it does not smoke all that well and wouldn't even make it into my top 10. It's all personal preference and I believe I'm a burger, fries and a Ford kinda guy versus a filet mignon and Mercedes type.