Microsoft is probably one of the worst offenders, especially in the past few years. It seems like they're actively destroying documentation and making it hard to find important information, so much that I often use archive.org instead.
Apple may be worse. They move documentation to the Documentation Archive and don't replace it. The Archive is a giant mass of "outdated", no longer updated documents, each assigned to 1 category. The Archive only has a title search now; full text search broke years ago.
All documentation on Help Books was archived, for instance. It's been 7 years since they've seen an update and they now contain inaccuracies – but there are no other official guides. Check out that UI: https://developer.apple.com/library/archive/documentation/Ca...
This is a technology that is still used. Nearly all of Apple's own apps have Help Books, including new ones like Shortcuts. Yet they have absolutely no official documentation on using that technology.
I don't know what it is that makes Microsoft so inelegant. Not only what you've said, but their APIs / programming environment in general is ugly and (I presume) unwieldy. Their apps (I just switched to Excel / OneNote / etc. from Google) have bugs that don't exist with competitors. The other day I couldn't use OneNote because my Internet went down (?!). Same for Excel, it doesn't reload immediately upon reconnect like Google Sheets did.
I don't get Microsoft. They're huge. They hire a lot of people. Their products are kludges.
backwards compatibility is a major reason why their APIs are so ugly. I always assumed that was a core company value. ironic that they turn around and break links to their own docs.
