I do not think the railroad is a necessary *evil* - railroads do some things much more efficiently and reliably than any other technology available today. It may not be the sexy thing anymore but railroads are vital.
Now, Microsoft is currently not seen as sexy, but there are things that they are doing well. Windows Phone is actually a nice product. It does not have the installed base or app selection or public mindset but from a usability standpoint, I would pick Windows Phone over Android any day (and especially if I had to pick one of those two for my wife or my mother).
The *buzz* is not with Microsoft right now but I think that may change - but even as such, I would not count Microsoft out. There is a lot of interesting and advanced technology in Microsoft R&D - it will just be a matter of delivering to the market things that the market gets excited about. That is not easy when you don't have automatic buzz about your products and your competitors (Apple) gets front page news coverage about rumors about future unannounced products.
I would disagree. You can easily find some nice phones for reasonable price. The Grados were always highly rated (and considered under-priced) with the 60s available for just around the $50 price limit (over $50 but not by much)
And, if you want an enclosed set, the Monoprice 8323 are hard to beat and would beat most other enclosed phones in the under $200 price range and they are under $25.
However, if you really want the best, yes, they cost - but "decent" is available, just not from consumer brands like Sony.
If in any problem you find yourself doing an immense amount of work, the answer can be obtained by simple inspection.