Re: Whats with all the masochism
My "line in the sand" was Vista. That's when I realised M$ were a bunch of fratboys playing with poorly thought out, but "new" ideas. Instead of standing on the shoulders of giants and improving things. Said goodbye to Windows as the OS on the metal in 2009 and haven't really looked back. Even though I earn my living from .net web sites, can't wait for my CMS of choice to run on .net core so I can ditch the Windows VM and Visual Studio.
As for the alternatives being worse. They're slightly different certainly, and in some ways much better, but I take your point on current office integration. Just needs a bit of investment ;)