Are (some of) these problems peculiar to Windows ?
Would people be better off purchasing the new Raspberry Pi 2 (quadcore Arm 7 + 1GB memory)
Yes and no. Windows drivers can always be annoying but generally once its working it should just continue to work. The same could be said on another platform. These have also been tested significantly more on Windows so we tend to know what will go wrong.
Cgminer primarily targets Linux not Windows. Ckolivas doesn't even test on windows at all(his windows builds are cross compiles).