If MS would have jumped into the mobile market full-force in 2008 I think they could have given Apple a run for their money. By the time they had a decent partnership with Nokia and released flagship quality phones in 2012 with the 920 and 1020 it was too late. Apple had five years' head start and had firmly established themselves as the high-end manufacturer with an entrenched user base and an extensive developer network.
Microsoft couldn't. People often forget, Microsoft was under the heavy thumb of the FTC and Justice Department at the time. The 1998 Consent Decree put them under constant scrutiny and examination by the Justice Department for violating the Sherman Anti-Trust Act for their bundling practices of Internet Explorer with the Windows operating system (using a monopoly in one market (the Operating System) to obtain the monopoly in another (the Web browsers)). Yes, this seems incredibly silly and irrelevant in 2018, and new kids these days don't know that there was no Chrome, Firefox, or others back in 1998; Microsoft strangled that new market back then. So the DOJ punished them for it.
Microsoft could not use their continued monopoly in the Operating System market in the period of 2007-2011 to strongly enter the new mobile device markets. They had entry, yes, but they couldn't promote it, they couldn't make technology acquisitions, they couldn't "bundle" Windows Mobile in any way, etc. They had to sit back quietly while RIMM took the market, and they couldn't do anything to compete against Apple.
DOJ personnel actually lived at Microsoft HQ in Washington on a daily basis and reviewed every contract and document that came through. When Microsoft bought Skype, that had to be reviewed internally alongside DOJ personnel and had to agree to conditions, including (you named it) trying to "bundle" Skype with Windows. Skype was now a Microsoft product, but they had to keep it separate. Same with OneDrive (nee SkyDrive).
The consent decree expired in May 2011, and that's why OneDrive could become integrated with Windows 8. By then, Microsoft was powerless in the markets, Apple took Microsoft's oxygen and wielded all the power Microsoft once had.
Apple played their cards well. But Apple did not do this on their own power. The DOJ destroyed Microsoft and made all the power up for grabs. RIMM could have taken the power (and they leveraged it for a while, but they ignored the long game), Nokia could have taken it but they were already in bed with a gagged Microsoft so that had its own limitations, Google... Google couldn't take it.
Google was already being sniffed out by the FTC in 2007 for their acquisition of DoubleClick. The last thing Google needed was more DOJ and FTC attention. Google bought Android in 2005, which was already on a bad approach and had to change direction after iPhone came out in 2007. So by time this all came around in 2007, Android wasn't even a meaningful thing. Yes, Android was "there" but it was a mess and it wasn't cohesive. It got its act together once it had Google's cash, tho. But the iPhone was already on the market, making waves.
The only player with any chance in the market, leading into 2007, ... was Apple. But again, the landscape was laid bare by the DOJ. Apple just moved in. They didn't "compete" their way into it like an organic market. I love my Apple, love the products, and I love my stock shares and investment.
We should thank the DOJ for giving Apple the opportunity. This is also why Apple does not want to be "#1" in the markets. If you are #2, you can do all kinds of sneaky things like bundle the browser, desktop OS, mobile OS, and wearable devices together and not have to play nice (give access to NFC chip, allow interoperability with the wearables to third party things) and you can do forceful things like hold a gun to Intel's head to make the chips you want, and piss on Qualcomm, strangle Imagination Technologies, etc. A strong #2 player can do these things. You can't do these deals if you are #1.
You can't use a monopoly in one market to gain the monopoly in another. Lest the fate of Microsoft be felled upon you.
