@swasheck One of the main reasons commercial software vendors don't like supporting Linux is that the kernel and glibc folks flatly refuse to commit to a stable ABI so it's difficult to ship binary-only software.
One nice thing about Solaris is that you can run binaries back to SunOS 4.1.
Most OSS of any consequence tends to get a MinGW32 port at some point, but the support can be hit and miss. If MS and Canonical were actually to team up and make a supported version of this then it could be a useful product.
@ypercubeᵀᴹ It's plausible. Emulating the GNU/glibc userspace is pretty easy on most kernels, including Windows. This just adds binary level emulation.