The views below are from my own personal experiences and may not be what "the next guy" experiences ...
Over the course of 2 years, I have put this to the test as I have been pondering the same thing after being confronted with the phenomenon "a pipe to die for". The results have made me change the way I smoke my pipes for good.
Pipes I smoked once a week did not perform as well (moisture, flavor, etc.) after 50 bowls as a pipe smoked daily (same bowl count). I arranged it so the daily smoker wouldn't be smoked until both pipes could reach the same bowl count at the same time. Then I switched the pipes around. The infrequent smoker became the frequent smoker and vice versa. After a month to a month and a half the characteristics of each pipe changed noticeably. I always smoked the same blend in the 4 sets of pipes (1 set = 2 pipes) I used and my results were consistent. All pipes were reamed lightly and cleaned after the 50 bowl count.
Between smokes I used one pipe cleaner in each pipe. First I cleaned out the stem and shank with both ends of the cleaner, and finished off my folding the cleaner and give the bowl a rubdown. I did not leave the pipe cleaner in any of the pipes.
The frequent and infrequent puffers switched characteristics little by little. After about a month and a half all pipes had changed over completely.
The tobacco used: Orlik Golden Sliced (the blend I have the most experience with)
The pipes used: Each set were identical pipes: example: 2 Stanwell Bulldog #32s, 2 Savinelli Oscar Tiger apple, and so on.
Also, all sets were initially either 2 new pipes or 2 newly reamed and cleaned pipes.
After this interesting and fun project, I concluded: If you smoke the same pipe day in and day out with the same blend and pay close attention to cleaning it properly after each smoke, you are going to have one heck of a smoker. If you smoke a given pipe "on occasion", you are likely to miss out on a few things. You will most likely get to experience what the blender intended with the blend, but I found that a well smoked pipe would intensify some of the flavors. I for one don't mind an intense taste of OGS (it's my desert island blend).
So now I pretty much smoke the heck out of my pipes. None of them have soured and none of them seem to have peaked yet. I dedicate pipes to individual blends rather than a specific group of blends. As a bonus, I no longer pack 3-4 pipes when I go on a trip, I just pack one
YMMV and (insert normal disclaimer here)