I think you underestimate the importance of context in all of this. You can't build any of these products well without knowing (deeply and certainly) users' patterns. Microsoft has no realistic way of knowing when it routes you to the wrong place...no continuous training data to let it feed and refine a personal assistant. Data products can be cool demos (see Siri) from a startup, but without both the starting dataset and the continuous feedback that you get by deploying these against real users and capturing the resulting behavior, I think they are quite limited. Continuous adaptation and learning is as important as the initial algorithm.
And while I certainly am looking into the future when I talk about cornering the market, I think it's an interesting question to ask how you compete against a company like Google that starts with this much user context. How can you build better experiences when they have the advantage in data, ML expertise, and the raw computational power? The incremental acquisitions of data and companies are not the issue...it's the web of connections that is valuable. And Google is not only trouncing Apple, their only meaningful competitor, in that race...Google is pulling even further ahead.
Microsoft search share is around 18% in US and a number of those searches are local (Apple has none of those). Additionally, they have a growing number of Windows 8 devices which they will be using for local/maps and train their models. I have used Bing maps and though it is not as good as Google Maps, it definitely holds up against Apple Maps.
To your initial question that if there is any company which could have built Maps or Siri, Microsoft is more than a good answer. You can try to get really nitpicky on this but it is what it is.
And while I certainly am looking into the future when I talk about cornering the market, I think it's an interesting question to ask how you compete against a company like Google that starts with this much user context. How can you build better experiences when they have the advantage in data, ML expertise, and the raw computational power? The incremental acquisitions of data and companies are not the issue...it's the web of connections that is valuable. And Google is not only trouncing Apple, their only meaningful competitor, in that race...Google is pulling even further ahead.