Problem: toolbars and menubars don't work for applications with 300+ commands. Solution: the ribbon.
Problem: Java is terrible. Solution: C# and the CLR
Problem: Online match-making for games is hard. Solution: Zone.com (RIP)
Problem: It's hard to write a song. Solution: Songsmith!
Problem: We're a large company that billions of people interact with, but is frustrating to work with due to a lack of transparency. Solution: Channel9 and employee blogging.
The issues with Windows 8 aren't "old problems", they're very new.
Thanks for contributing here. I really appreciate your efforts to help us understand what Microsoft (people) are like.
Though I have to say Songsmith?!?!? LOTF! No doubt its is super sophisticated tech and is amazing in what it does but so was Microsoft Bob in its day. That commercial is so absolutely chalked full of nerdy goodness...
As for the Windows 8 problems I'd agree they are new but many were also predicable long before release. While there are merits to Sinofsky's approach I think this time it backfired.