Is Microsoft with its new identity running the risk a Gap like identity disaster?
I appreciate simplicity in design. I like the direction Microsoft is going. But there is such a thing as "too simple". In branding you must create a good balance between being uniquely recognizable and being simply iconic. There is a danger that the new four simple colorful squares are too generic to serve the company's re-branding efforts well.
The red (orange), green, blue and yellow color scheme is a very common theme in logos. Google with Chrome one their closest competitor uses it too. The old Windows logo had these colors prior to Google, but with the opportunity of rebranding MS perhaps should have tried to move away from their competitors instead of blending in.
The shape and structure of the four squares is also a very common in logo design. A simple Google Images search revealed dozens of similar company logos. There are several similar logos here on StockLogos too like this one.
Microsoft has lot of money to put behind this identity, so if they do it right, they can probably pull it off.