Don't get me wrong. I love Wine.
I love Wine for one particular reason. For ten years or more it has made it possible to run LTspice on Linux. LTspice is a pretty sophisticated schematic editor and circuit simulator. http://www.analog.com/en/design-center/ ... ators.html
and it runs perfectly under Wine. It's almost as if Linear Technology goes out of their way to make it so.
If you are really perverse you can write GUI apps using the Windows API on Linux using libwine. Without ever seeing a Windows machine. Yes, I am perverse enough to have done that.
But as they say "Wine Is Not an Emulator". It's an implementation of the Windows API. Which may or may not be complete enough for whatever Windows program you have.
Moving that to a whole other CPU architecture, like ARM on the Pi, is whole other can or worms.