Some history from RSDancey apepars on page 7 with a brief follow-up by you again:
and he gives his opinion on technology in ttrpging (back in 2014) down at:
with musings on MMOs a few posts below that and another on the OGL a bit after that.
The following from him seems pretty relevant to today, especially the last paragraph:
"If there's a meaningfully large number of people who will jump through hoops to play an "old school" retro clone of 1e, that's critical information that Wizards wants. There's very little Wizards could do to uncover that information short of letting people just make whatever the hell they wish, and then seeing what sells and what doesn't.
Wizards should have the "retro-clone" market under a microscope, at least to the extent that they can figure out if it's real, or just a small group of really loud people. If it is real, that is something worth knowing. And if it's just a small group of really loud people, that's something worth knowing too.
If the company threw cease & desist letters around at anything it found offensive or "dangerous" to its intellectual property, it would squash the kind of innovation required to explore all the market niches, and scratch all the itches. And it wouldn't likely sell one more D&D book, or generate one more dollar of D&D license revenue. It's all downside, and no upside.
Eventually I think Wizards will want to clear the ground and fight to define its rights to copyright roleplaying game materials. The recent string of court cases in the US that are expanding the concept of copyright to "worlds" beyond "works" is all in their favor. But they're not going to fight that battle over OSRIC, for goodness' sake. They're going to fight over something worth tens of millions of dollars. The target for that fight doesn't even exist yet, but if it arises, Wizards wants to keep its powder dry. Remember that copyright, unlike trademark, does not lose enforceability if it is not defended"
-Dancey in reply #116
There is more by him later in that thread to. Feels worth a read to those interested in the history of the game who haven't read much up on it before (ranging from rumors of how well things were selling to 4e to Forge).