This might be a stroke of genius or an utter idiocy, you judge.
I seem to understand that the major shortcomings of wine are with the dlls because not all the libraries are emulated and not all are emulated seamlessly (no guilt whatsoever, I realize that the wine guys are doing their best).
So here is the idea.
When installing wine, or from the libraries configuration menu at a later time, there could be an "import original libraries" option, I choose it and I supply an original Windows cd/dvd that I have lying around (we probably all have a couple, even if we just use them as glass coasters).
Then wine runs trough the cd, borrows what it needs to run smooth with direcx and everything else and configures itself.
Final step, playing that damn brand new game or that damn cad application we need so desperately.
It would not exactly be the ideal solution to bug #1 but for somebody it would be way better than dual-booting.
P.S. I do not even know if this would be completely legal, if not perhaps it could be implemented as a separate script.