Regarding the timing of older editions (3E/3.5E) going CC.
Bob World Builder Interview (full version)
Starting at 18:18:
Bob: So let's say just to maybe, like, narrow down on this a little bit as well. You know 2024 - huge year for D&D. Um, is there any guess or, like, plan that by the time 6E comes out, is that when all these SRDs will be in Creative Commons, or do you think it'll be something that happens later down the line?
Kyle: I think it'll be, uh, in in-flight updates. So I think that as we you know we obviously have to publish rules first before we put them in the SRD. But you'll get to see some of the rules changes we're working on as we do the play tests for for One D&D, and so you'll have some idea of the rules changes that are coming up. And we expect the community will tell us, "hey you need to make sure this makes it into the SRD," just in case we're overlooking something.
Bob: Yeah.
Kyle: And then when the actual rule books are published, we'll follow that up with an SRD update.
Bob: Yeah I guess, uh, I-I also meant for those older editions.
Kyle: [spoken with a "for sure" tone] Oh yeah.
Bob: You think in Creative Commons—
Kyle: Yeah.
Bob: —by 2024 or end of 2024?
Kyle: Oh I think that'll happen this year. I mean, we just have to do our homework and do the review. It's, you know, there's no particular reason to delay it other than the work.
Bob: Okay.
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Regarding other old editions going Creative Commons.
Nerd Immersion's interview
Starting @ 20:55:
Ted: To that point, just to touch on the previous SRDs, I know obviously one of the big ones that was out there was the 3rd Edition one. Is there plans to possibly go further back, or even touch on 4th possibly, if people are still looking to to do things like that?
Kyle: Yeah, I don't see why not. I mean, other than the work involved.
Ted: Sure.
Kyle: You know, it's all, like, got to look at it, figure out what's the perfect thing to put into an SRD, for editions that may not already be in SRDs, we'll have to create SRDs for them, which is a fairly, uh, extensive process. And some, honestly some of those old editions, wow, the files are... [laughs]
Ted: Yeah. Sure, I can imagine, yeah. [smiles]
Kyle: It might just be a logistical problem, it's not a strategic problem. Anything that would hold us up would be more logistical than strategic.
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EDIT: So you're correct on the latter point about older editions being only considered—which I'll note is exactly what I said in my earlier reply—but he definitely did give an estimate of the 3/3.5 SRDs going CC sometime this year (and spoken with quite a bit of confidence, I might add). In any case, he is aware that there is interest in the older editions and seemed amenable to exploring it, assuming logistics aren't an issue.