MS Office and it’s UI inconsistencies (where’s the button I need?). While Word and PowerPoint technically have good tools for managing styles, the interfaces steer users to use manual tweaking to the point where I don’t think I’ve ever seen a clean document. And after a few copies and pastes between documents, you now have 100 styles that will never be managed again.

Shared folders are a nightmare for version control, share point is inconvenient and slow. One Drive works OK and finally allows collaboration. Azure is good for some other use case (probably, never used it). So for a typical company, MS should guide companies to transition to use OneDrive and keep things in one system? No, single sign on, IT gets sold on how easy it is to manage all tools, everyone gets every tool. And for good measure everyone gets teams, surprise you’re using share point even if you don’t know it and now all your confusing v2_final files are spread out in 5 places.