The OSR has undergone what I think is a radical transformation, stepping into a "second wave" that has been building gradually over the last 2-3 years. Here comes the necessary blah blah disclaimer about what I mean by OSR. I am one of the guys who means the entire community, not just the publishers. 'Nuff said, this isn't about defining the OSR -- if "OSR" hurts your head, just substitute "the old school gaming community that takes advantage of electronic communication." That's the group I'm talking about.
Okay, what is this second wave? People have been talking about second-generation retro-clones, which is a misnomer because the whole point of what they mean by "second-generation" is that these games are not clones ... in any case, this is not where I think the actual second wave is taking place. It's a good thing, for people to be producing innovative rules that draw upon the structural design goals of older gaming (as opposed to actually restating the out-of-print rules for preservation, cost reduction, publication support, or organization as the retro-clones do).
If they're the same thing, then the second generation of retro-clones happened before the first: Castles & Crusades broke the finish-line tape for using new game mechanisms in an old school game long, long ago. Whether they did a good job, which some people debate, is a completely different question -- they absolutely were the first to undertake the project of using different rules to target old school design objectives. The SIEGE Engine was a very new approach to target numbers, used in the context of a game with few rules and lots of roots in AD&D.
The two undertakings are quite different: one project is to build a better mousetrap, the other (retro-clones) are just trying to take the original mousetrap back off the shelf and get it working again.
Anyway, I'm not trying to start a terminology war, because goodness knows I think "old school" is too vague and lots of people argue with "Renaissance," and I think that whole sort of academia-of-last-week's-developments tends to miss the point. I bring it up only to emphasize that what I'm talking about as a "next step of the OSR" is completely different from the second-generation "retro-clones."
I'm talking about actual gaming.
Castles & Crusades, as the first simulacrum game, and OSRIC as the first clone (yes, I'm ignoring Hackmaster, I know) were both primarily about publishing. C&C was a vehicle for playing Castle Zagyg and allowing Troll Lords to publish AD&D resources under their proprietary brand name. OSRIC, although it morphed in a major way, was primarily about creating a shared brand name that would allow anyone to publish AD&D resources. C&C used purely the OGL, OSRIC added the use of some copyright law outside the OGL, but they were both oriented NOT toward increasing the number of gamers or building communications among gamers. C&C was to create a product line, OSRIC was to create multiple product lines.
Products. Resources is probably a better term, but the bottom line is that we aren't talking about gaming, we're talking about resources. As it happened, OSRIC accidentally turned out to be something that was used as a tool for introducing AD&D online to new players, but it wasn't planned that way and didn't affect the existing community of gamers. Actually, come to think of it, C&C also brought a lot of 3e gamers back to old school gaming too, although by a different process. These games expanded the community, but the way they enriched it was by increasing the number of resources.
Then come the conventions. GaryCon was the first self-described "old school" convention. (actually, this might have been TrollCon -- not familiar enough with the way TrollCon works to have an opinion on that, so I'll stick with GaryCon for the purpose of this discussion, but I could be wrong). There's no question that the critical mass for GaryCon came from the internet, and the ability of the internet to spread the word to a pre-existing community. Which is why I call it a product of the OSR as I define it. The primary driving engine of the OSR is the internet and the communication that it permits.
And then came North Texas RPG Con. Another old school con. A powerful one, with lots of attendance given that there was already another (and possibly 2 others) con out there with the same target audience.
What you see with the conventions is GAMING. Not resources, but actual gaming.
And now ... ConstantCon. using the internet to gather people together for online gaming. Yes, that has been a constant feature of the net for a long time, but this is the first umbrella organization for it.
So I submit this: I think there is indeed a new wave in the OSR. But it's not something that has to do with product-creation like the retroclones or the more recent "new-rules, old design prnciples" games. It is a larger sea change, because it is a new set of steps that are being taken toward gaming rather than toward gaming resources. Gaming resources are awesome, but actual gaming is obviously the real thing that the OSR has been striving towards.
Rebuilding a convention scene for older games, whether the convention is face to face or online, that's the real new wave that's going on here.
Next step after this one is to increase the number of people who can find face-to-face players nearby for regular games at home. But I think we'll need teleportation technology for that one.