It's entirely possible that the days of WebmasterWorld are on the horizon. Or maybe not. Brett said a mouthful in the OP, but I would offer the following:
- Not changing is one possible course of action. It may not be right,but it could very well be. I'd say there's probably been 3, maybe 4 turn overs of posters cycles here right? remember sugarrae? Shak? Darren? And probably more before that that I wasn't around for. The forum's still here.
- Changing and incorporating social media may be the way to go. Personally I see it as either a fad, or undefined (don't know where its going, but it's not there yet) and wouldn't chase it because when social media becomes irrelevant, then the site becomes irrelevant. But I don't have a good handle on it.
- Changing but not incorporating social media. Personally I like the idea of a more updated forum with more features plus some ads, a directory, classifieds. Let me rephrase that - quit screwing around with social media because it does nothing - focus on stuff that matters to us from a business perspective. give me more resources - does not have to be in a social media format. What's a real, quality controlled SEO directory worth? I don't think such a thing exists - WebmasterWorld could possibly make that happen, just as one example. in other words, focus on the information and resources not on how it's delivered. There's a dozen gimme's in terms of expansion that WebmasterWorld could be doing that aren't being done well elsewhere.
The two other areas I see out there that could be bumped up somehow are affiliate stuff and domain stuff. I don't know much about either, but see opportunity there.
And of course, the question is, where's the money - in the forum or the conferences? Pick one, and use the other to feed it, make some plans to make that happen.