The comment was about the last decade? Seems kind of irrelevant to bring up an obstacle from the 90s.

> Over-monetizing their dev tooling was a significant contributor to Microsoft's loss of dev mind-share over the last decade.

Also at that time you could for about 60 dollars buy 'the win32 bible' which had pretty much every call you wanted in print form. Also about 50 bucks got you the CD with the docs. Only when you went to the 'I want MS in a box' MSDN that you paid more. MS dominated in that market in the 90s because they had tooling that was wildy cheaper than most of their competitors on other machines. Sun/IBM/Apple easily priced their docs in the 20k+ market. I bought many of these docs for these different archs at the time. MS was by far the cheapest of them. Borland and Watcom had 2 different setups with and without docs. You paid accordingly (usually 100-150). Also once the internet came around MS put its docs up on the web pretty quickly. They were about equivalent to the CD's. I would say around 96/97 they did it. I have not paid for MS docs since. I paid a few times for MSDN as I would need a lab of machines and ACLs were dumb expensive.