I think the interface is simple, because it's quicker for a vm to draw, scales better to weird screen sizes and pixel densities and compresses better on a remote desktop connection. Maybe MS is betting the farm on the cloud and want the best interactive experience when the installation count of the OS peaks in 5 years time.
Don't the H.R. people hate "jack of all trades" people, too?
Yes, but I'm convinced that recruitment agents are even worse. If you don't fit their template, they butcher your carefully structured resume into something that basically says: "This guy has been working for x years, but we're not actually sure what he did in that time." If it's all just buzzword soup to these intermediaries, the connection between the type of problems that the candidate has experience in and the need that the prospective employer has gets lost.
Then there's also the fact that some industries, like banking, believe that their domain knowledge is so absolutely unique and special that nobody could possibly transfer valuable skills from a different sector.
iTunes is 2 Episodes behind.
Talent does what it can. Genius does what it must. You do what you get paid to do.