Everything MS has is pretty much based on the future direction they see things going, which is good in many ways.
Always on connected multi-purpose living room box.
Tablet focused OS.
Cloud services, both end user and business.
They are "failures" in the current environment, but move forward to v2, 3 or 4 of each, when they have been improved, and who knows.
Meanwhile they are still making lots of profits with things as they are now, as "failures".
It should be pretty obvious to most people that most MS products are forward focused right now, for once, and because of that, they aren't quite right, like the whole UMPC crapfest, or old PDAs/tablets, which were too early and pretty crappy.
If you don't believe that integration and always on and tablets/portable devices are the future, you're living in another world. MS is just doing things slightly too early compared to the maturity of their internal projects. e.g. Xbox One might be too soon, and Windows 8 wasn't close to a perfect product, although the idea makes sense.
Its technology convergence theory and I think its impossible to converge the desktop onto anything else, be it phone, or touch screen pads/phones etc. You might check your email or download apps on a tablet but you aren't going to sit down at your tablet at the end of the month and pay your bills, write letters, make resumes, etc. on your tablet.
If anything what we have seen is a bunch of divergence lately. People get TV but get it several different ways (netflix, HBO, cable, OTA, etc). People check email/messages/call but do it several different ways (wireless phone, desktop, tablet, skype, VOIP home/mobile phone etc.). People play the same games, but do it several different ways. (Steam vs consoles vs buy physically)
Trying to converge everything into one... we'll see how it goes but I think its a mistake personally. Microsoft is going super all in on this strategy. They are integrating the new word and office to be more cloud-like. Like you'll have your one "Windows Live ID" to login and hop on word, watch movies, store files, play xbox, login to windows etc. Seems to be what they want, I think its a pipe dream. They aren't in a position to congregate everyone like that. They aren't well known in media, everyone is using fragmented versions of OS's, fragmented versions of word, etc. They want to be like Apple with a 1-2 year upgrade cycle and almost full compliance at a time when people are going 5 years without buying a new PC. People still bitch they can't open .docx... Apparently we are all supposed to be using touch screen windows 8, there is a huge disconnect of reality vs what Microsoft wants.
I've got Vista, Win7, Win8 as of late, and I pretty much try my best to make them work like XP did. Start menu app anyone? Have any of you used Windows 8 much? Its on a laptop, I dread using it. I've actually got the newest version of word 365, etc. It looks funky when you load it on a desktop because its made for a touch screen. People are probably hammering away on their 3 year old KEYBOARDS about how great all this new stuff is while running windows XP/vista/7.