I think some families of saws were more renowned in their smaller displacements. It seems like a lot of people actually prefer the powerband of 266 vs the 272.
I myself usually prefer the larger displacement, as I can usually mod it to run how I want. A personal example of this, would be the whole 044 vs bb/hybrid debate. If we're talking un-modified cylinders, the stock 044 is much better. However a little machine work and some grinding, and I'll take the bb or the hybrid every time.
We forget that not everyone has a chainsaw fetish like most of us do. For most people, it's mostly about a saw that's "good enough" and at a certain price point. Locally...even though the 362 is still a "pro" saw in Stihl's line up, it seems like they are really popular with non-pro guys who want something better than a 291/391, but don't want to pay for a 400. They can put a 24" bar on it and it'll buck all the firewood they need.
It's not until it gets to those of us who are saw weirdos and/or heavy users, that we really care about getting the "best" saw in that class.