Probably Scott Guthrie initiated that. As some nobody I once emailed him directly because I'd discovered a bug in some framework thing with a reproducible example. He actually replied and cc'd in the relevant people at MS and after a short while there was a workaround and a fix and a KB article or something (it's so long ago I barely remember). Impressed? absolutely. MS still have some pretty good and accessible folks, and I'm a huge fan of Scott Hanselman who's a great brand ambassador for DevDiv (and not beyond a few self-deprecating MS jokes about the company's past).
Documentation pages that showed a method's signature with no explanation of the function or example usage. So many times I'd look something up only to find the method name parroted as a full sentence; and those method names were often obscure to the point of meaninglessness.
Anything that was available online, official or not, was inferior to that. I'm not sure if it was deliberate, but it significantly hampered the utility of pirated copies of Visual Studio - since MSDN docs would require a lot more CDs than the software, most warez releases stripped them out. And in the developing world, where such pirated software is readily available on physical CDs sold by street vendors, they would usually be priced per CD regardless of what's on it - so a complete VS+MSDN bundle would be a lot more expensive, and thus in relatively low demand, and not widely sold.
It's a hard sell to tell an IT decision-maker in a different team/group that you need to configure things "just so" (think TechNet versus MSDN for configuration/operational articles) when all you have to point them too is a non-official blog post...
(Don't even get me started about the quality/out-of-date materials for things like Dynamics 365...)
It got so bad that a VP ended up making a pronouncement, declaring a war on broken links. He announced a multi-year plan to reduce and eventually fix all the broken links on MSDN. This was the vacuum that was partially responsible for the birth of Stack Overflow.