I think a smaller ring usually delivers sharper flavors, while a larger ring delivers smoother flavors. I think that's a real fair generality.
If you find a cigar you like, use that idea to move up or down in size to find what you enjoy.
I also think a larger ring is going to develop flavors and nuance that you'll never find in a small ring, because there's just not enough time and tobacco to build to that crescendo.
If I'd have stuck to just one size, or get into a small ring or large ring habit, I'm going to miss a lot of really good stuff along the way. I try to mix it up as best I can, but it's sometimes hard to devote all the time necessary to a big ring to get to all the goodness that an hour and a half of smoking can create.
The difference between an Anejo 46 and a Shark comes to mind. Two similar, but very different experiences.
