Dragons Are Real has an RPGaDay post called Evolve that ends with "I wonder where this will lead us in the next 45 years…I may not be around to see that but I think the hobby is save and will continue to evolve." I've thought about this subject for some time and it will be interesting in the coming decade or two as the original grognards who started playing in college or younger start to retire and suddenly find they have lots of free time again.
I think a large part of the OSR has been the cultural divide between the young (who Wizards courted with increased complexity in 3e and 4e) and the old as grognards who have hit a spot in their careers that allowed for more home life and a returned to the hobby (they wanted to play what they knew instead of starting over). The number of new gamers will just increase, possibly ten-fold, as old timers start to retire.
I suspect the number of players will increase as well. Folks in a retirement home are less concerned with looking cool than they were back in high school, they might be a lot more willing to give the game a go.
Selling Dragons
Dungeon Fantastic has a post called Selling Dragons - did it come up in your game? in which he talks briefly about just that. I've never had players try to subdue a dragon but then the opportunities have been few and far between as I have always preferred low level play. Still the post got me thinking about how much fun it could be to have a campaign in which the characters go out and acquire rare beasts and monsters for the arena, or for the Wizards school, or whatever. They could be told where the things are by experts, and be provided with an appropriate cage and some bits of knowledge (some accurate, some sketchy), and then off. They have to track, capture/subdue the thing and get it back to get paid. And of course there are those that would want to kill the beast in revenge, and other groups interested in the cash to complicate things even further. Could be lots of fun.
Monty Pythons Goblins
I was reading through blogs and some commenter posted some images from the East German version of the Hobbit. The images were drawn by Klaus Ensinkat and I find them a fascinating as they were created before Rankin Bass and the Brothers Hildebrandt and Peter Jackson solidified the images of different creatures into our collective memories. The first are the three trolls.
The second are Orcs (or Goblins) in pseudo-Samurai gear.