Finding the best of your pipes for a blend shouldn't be a major dilema. Although some tobaccos tend to smoke better in one pipe over another, a pipe shape or size change is not able to make a blend you don't particularly like suddenly taste good; however, you may discover that a specific tobacco blend just seems to match a certain pipe or certain pipe sizes and shapes best. The reason is often burning characteristics but sometimes it's simply a personal preference. At least in my case, I have two or three pipes dedicated to specific blend types, such as pipes for English, others for aromatic, others for Burley. Interestingly, these are not all the same size and shape and assigned to a blend type based on those characteristics. It has been more of an evolutionary process, like so many aspects of pipe smoking; they are personal preferences developed through experience, mostly by fiddling just to find what works for you. In fact, it may be something you just stumble upon while getting familiar with a new to you blend.
General guidelines do exist, but these are personal because they are based on ones own smoking style.
I tend to put flakes in smaller bowls, but that is due to my inability to smoke large quantities of tobacco so this may not apply to others. I like Virginias and many aromatics in larger bowls, especially if ribbon cut. Other than that, I have a number of non dedicated pipes where I just throw in some tobacco and see what happens, usually with good results.
I conclude that although there is some merit in pipe and tobacco matching, it is very subjective.
But why take my word when you can read an article by
G. L. Pease