Thinking back to the boom of the nineties, I remember smoking Fuentes, Padrons, ERDM (NCs), HdM (NCs), some vile things that Nestor Plascencia put out, and some Cohibas that I had a line on from Spain. Those are the only brands I can still recall. Whatever else I smoked at that time has faded from memory. Probably faded from the market as well.
Personally I don't think we're in another boom. Back then, smoking a cigar became something of a fashion statement. People that really didn't even like cigars had them hanging from their lips. I don't see that today.
While most of the boom cigars are gone, I would imagine the people that produced them are still around. They're most likely still producing boutique cigars today for anyone with the capital to come up with something. I suspect in another twenty years, they or their kids will still be producing cigars as well. While some brands stay and others come and go, I think the guys that grow tobacco and produce cigars tend to stay fairly constant.
As far as the 'special' stuff, I think the limited editions are more marketing than anything else and will always be around. People will always chase things in short supply. It's part of our nature. We just can't help it.
While my crystal ball is kinda cloudy, I think the game changer in the future might be if Cuba opens up, and their cigar people start up new brands, form ventures with other cigar manufacturers, and/or Cuba starts exporting raw tobacco. That could shake things up in the cigar world.