The biggest miss from Microsoft is failing to give the typical consumer what they really want. They were late to the phone and fell flat when they got there (I know 1 person who has a Windows phone). They were late to the tablet and instead of bringing what people like about the PC to the tablet (power, file systems, flexibility), Microsoft decided to bring what people don't like about the tablet to the PC (limited screen size, lack of UI configuration options, swyping through screens to get to what you want).

I have been reasonably happy with the SQL Server advancements in the past decade, especially with the add-on products. SSIS and SSAS were huge. I would say that SSRS has a long way to go to provide more visually appealing online reports with cleaner drill through capabilities).