"A reputation for flakiness risks long term damage to Microsoft in the enterprise."
Well, Windows has been various flavors of "flaky" for a good 25 years now, but that didn't seem to hinder BillG from becoming the richest man in the world. Exchange and Outlook have both always been pools of pain for users and admins the world over, but companies continue using them. How many times have Word or Excel taken a crap on their files, but nobody in serious numbers is talking about moving to Lotus or WordPerfect, or even OpenOffice.
Truth is, everybody knows Microsoft's software is complete crap, but it's just barely good enough to usually work, and Microsoft's past heavy-handed monopolistic practices made sure there aren't any serious contenders anymore even if folks DID decide to jump ship. Apple probably should have ascended to the throne - they had the talent, the money, the cachet, and the ambition, but inertia was never in their favor. I've been waiting for Linux to take over the desktop for, oh, 17 years now, and while it has made inroads, it's sadly suffering the same inertia that kept Apple at bay.
Remember - Microsoft=Windows, Microsoft=Office, Microsoft=Windows-Server and now I guess Microsoft=Xbox. Anything outside of those four things (maybe MSSQL Server too) is just a dalliance for MS - Azure, Office365, Windows store - those are all just for the "here and now", and could go "poof" at any moment at the whim of MS.
Just my 2-cents worth. Flakiness is part of the Microsoft landscape.