Just for fun, I snaked the RPG Blog Carnival questions regarding "The Future of Roleplaying" from Roleplaying Pro and answered them with the OSR in mind.
What games do you see emerging as the big players in the near future?
Mythmere Games. Between S&W and Knockspell Magazine as well as their support for the OSR, I can see their snowball getting bigger as it rolls along.
What companies should we be watching out for to release the next big product?
Brave Halfling Publishing is beginning to do everything from old-school to 4e and are now top sellers on RPGnow (for classic-type RPGs).
However, Chaotic Henchmen Productions made a big splash with Guy Fullerton's Dungeon Module F1 - The Fane of Poisoned Prophesies.
One of these two companies will produce the next adventure everyone will be blogging about.
How will technology become more integrated into roleplaying games?
It already has or else most of these indie publishing companies would not exist (including PRG!).
What industry writer do we need to be on the look out for?
James Edward Raggi. A quality writer and a hell of a chance-taker.
What blogs do you see exploding into becoming the next big thing?
I really don't know. The few I frequent include Grognardia, Greyhawk Grognard (I'm a fan of his Castle of the Mad Archmage), and LotFP, among others.
What do you see for the future of the industry?
I see a paper-thin, superficial coating of "you're not playing it right" with a meaty center of fun-for-all house rules, picked from the various RPG faves. People diving into "old-school" playing will want to get EVERYTHING - Labyrinth Lord, S&W, OSRIC, BFRPG. etc, as well as their supplements - and take what they like from each (while using one set of rules as the system of choice).
I would also like to believe that these house rules will result in more fan-produced material.