I agree with the way you have framed this. I think we are saying basically the same thing (you use "law" where I used "statute"), and are trying to focus on who has the benefit of what private rights against WotC, which have been created by entering into licences or sub-licences with WotC.The interesting question becomes if the new SRD is designated "Open Game Content" under the OGL 1.1. The question then becomes, does the OGL 1.1 only apply, or can I use the OGL 1.0a for this Open Game Content? And that isn't actually particularly obvious. The OGL 1.0a is not a law; it does not automatically cover material that is simply called Open Game Content. The new "Open Game Content" was released under the OGL 1.1, not the OGL 1.0a. But if I'm already a licensee under the OGL 1.0a, and WotC releases something they call "Open Game Content", it is possible that I can use the new "Open Game Content" under the existing license. This is particularly true since WotC drafted both licenses, and ambiguities in contract law are supposed to be resolved in favor of the non-drafting party.
I agree with @FrogReaver's analysis: Jane is breach of her contractual obligations to Bob under the OGL 1.0, as she has not complied with her obligation to provide a royalty-free licence for the use of the OGC. Under the OGL 1.1, royalties are payable (on a conditional basis).So, Gamer Bob writes an adventure and sells it under the OGL 1.0. Makes beer money. Sweet!
A few years later, Gamer Jane looks at some Open Game Content in Bob's adventure, thinks it is cool, and puts it into her sourcebook under OGL 1.1. She hits the lottery, so to speak, and makes over $750k. Good on ya, Jane!
Then WotC knocks on Jane's door, and Jane pays WotC a royalty on using the D&D game engine for her creative work. She then goes back to her desk hoping to catch lightning in a bottle twice.
I don't see how the sky is falling here. Jane doesn't owe Bob anything, OGL says she can use his stuff royalty free. Bob doesn't have to pay anything. Not only did he not make the $750k threshold, he published his deal under a different version of the licence a long time ago. WotC isn't paying anybody anything, people are playing in their sandbox, as it were.
I'm not seeing how the sky is falling here.
This is the basis of @estar's concerns, as I understand them.
I personally have no real stake in the issue of whether or not WotC's plans lead to multiple, separate, OGL communities. (Whereas this is an important issue for estar.) I'm just commenting on the legal analysis.