People hate Office? I don't think I've seen any significant hate for Microsoft Office (but I personally hate LibreOffice).
> calendar has hardcoded top-down management assumptions
What? Where? Is this about the list of other calendars defaulting to showing people under the same manager?
> information is siloed to only meeting participants
You can configure it to show meeting titles to everyone (the company I work for expects everyone to do so), and the new Outlook even showed me the meeting description and participants when peeking at someone else's calendar.