Howdy Pipebaum and great thread starter!
Without question, the same blend will make a different presentation in different sized pipes. But, to say that one size pipe will smoke better than another is not a theory that I subscribe to. Rather, just a different taste presentation. A particular blend in a small bowled Castello, IMO, will not smoke any better or worse than a blend in a larger bowled one unless such a presentation suits your own tastes.
I'm totally with misterlowercase on the V shaped bowls and so are a lot of other folks. The general thought is that conical V shaped bowls will present a stronger taste as the tobacco is consumed. A U shaped bowl (such as found in billiard shaped pipes), will, generally speaking, maintain a more uniform presentation of the leaf from top to bottom. That has certainly been my experience over the years but others may have a different opinion.
For a fun test (and one I have performed many times), is to take a couple of pipes from your rotation that you know really well. One with a V bowl and the other with a U bowl. Then, take a tobacco that you also know well. Smoke the blend in one pipe, wait a few hours or even a day or two, and then try the same blend in the other pipe. See if you like the overall taste presentation better in one or the other.
To complicate matters; I've found that different blends perform better (for me) in one shape or the other, but not all blends perform better in the same shape bowl. As an example; I appreciate the taste of McClelland's 5100. It is a delightfully sweet Virginia but doesn't really have the stronger taste or strength that I gravitate towards. To me, 5100 is a bell ringer in a pipe with a V shape bowl as the flavor concentrates as I work my way down the bowl due to less air space. So, when I get a craving for 5100, I always reach for either a Dublin shaped Moretti that I own or a Dublin shaped Kevin Arthur that smokes great. Both have dramatic V shaped bowls and the 5100 really sings in both of them.
Again, great thread starter and I look forward to hearing from the other great folks here regarding what they have discovered regarding differences, if any, in bowl size and shape.
Pipestud