I've had a love/hate relationship with MS for a long time. On one hand, the things they did with both DOS and Windows have been amazing. Even though neither were original concepts developed by them, and neither were perfect at any incarnation, they've done a phenomenal job expanding the use of PC's to every part of society (and yes I realize macs were considered easier to use. I used them extensively in college and always preferred PC's). They XBox line has been great, despite everyone thinking they'd fail at the beginning.
But then they've done so many stupid things along the way that just drive me nuts. They are so focused on a few core concepts that they miss the potential on so many others because it doesn't fit into those core concepts, or because are so paranoid at cannibalization that they can't fathom integration. Some of the products they have worked on that missed their potential:
1) Surface - I realize it exists in the business market, but it has/had so much potential in the consumer market too.
2) Zune - My wife had an original generation Zune. She loved it. It was far superior, technologically than the iPod at the time, and the software was as easy to use, and more format friendly, but rather than integrate it properly with your PC, XBox, etc., they tried to segregate it. Heck, even PlayReady videos you find on DVD+DigitcalCOpy discs, which are a MSFT technology, wouldn't play on it! They should have integrated all their media so that it was platform agnostic. Buy it once, play it anywhere. You should have been able to buy a video on XBox live and automatically have it available on your Zune and PC. And they should have run it as a loss leader to undercut the iPod.
3) Windows Media Center - I run an HTPC for all our media needs in the living room - Cable, DVR, DVD/Blu-Ray, Music, online video. It's awesome, but it took 5 YEARS to get a cablecard expansion card so you could watch live TV on it. It's also an unfinished product, requiring a lot of 3rd part add-ins that complicate things, so when it does have a problem, its a massive PITA. Again, they should have integrated it. You still can't play most content bought on XBox Live or Zune Market on it. They could have dominated the living room like nothing else. The XBox does a nice job on some things for that, but it can't do what a dedicated HTPC can.
4) Courier and Win7 Tablets in general - Win 7 can work beautifully on tablets. I've seen a couple companies that developed skins for it that make it comparable to the iPad, both in the general GUI and application specific. I was pumped waiting for a good Win7 Tablet to come out. The idea of having something that I could dock and use as a normal PC, then undock and take with me as a Tablet, with all the same programs was amazing. Instead, we get virtually nothing.
I fear that Google, with their obsession on data-mining ultimately is going to follow the same footsteps as MSFT.