My experience kind of parallels yours, Todd--I first started smoking cigars in the late '80s, and notice a lot of those same boom-type patterns today. Wayne makes a good point about the speed of communication. I think that pushes everything a lot faster. I'll still smoke some of those "older" 90s brands--HdM and Punch. Their products have stayed consistent, maybe not as adventurous as some of the newer lines, but I know what I'm getting.
I see similar trends in craft brewing. Lots of small breweries popping up, trying to capitalize on the current trend toward more flavorful beers, "quality" beers. Some of them will last, some of them just seem to be pushing the extreme brewing envelope. Some of them will probably get bought up, products and tastes will change, etc. It's also putting a strain on product supply--this is the second year in the past 5 or so where there's a worldwide hops shortage. Limiting for business overall, frustrating to small (home)brewers like myself. That's probably the same kind of thing that leads to the LE cigar production as well. Make hay while the sun shines. Or, in this case, cigars.
Very thought provoking contribution, thanks. On a humorous note, my mind used an Andy Rooney voice to read your post. It was funny in my mind