That's kind of cool, if a bit perverse. A much more practical solution is a headless Virtual Box running Ubuntu, which you SSH into and can install anything via apt-get, etc... I recently started using this on OS X (via Vagrant) and it's super useful, for instance having access Linux LaTeX packages instead of having to deal with MacTex (MacTex is probably fine, but the 1.5 gb download was crawling for me, while `apt-get install texlive` took a few minutes) For Windows I would imagine it would be even more useful, since fewer Unix tools are immediately available. I think I would probably prefer this to Cygwin, which was always a bit weird for me.
This works great on Windows as well. I use Putty to SSH the Virtual Machine. I develop linux applications on my Windows machine seamlessly. It's really better than Cygwin, but I use Cygwin for some stuff like git. I also managed to install node.js with Cygwin, which is kind of cool!
"Cooperative Linux, abbreviated as coLinux, is software which allows Microsoft Windows and the Linux kernel to run simultaneously in parallel on the same machine."
Check out Windows Services for Unix. You'd be surprised what works out of the box with it. It also enables case sensitive access to NTFS volumes, which can be really useful.
This focuses on int 0x80, which is the old method; it's been replaced by the sysenter opcode, which is faster on newer chips. (This has been the case since Linux 2.5, and Pentium II+ processors; it was apparently first noticed on the Pentium IV.) Would this basic method work with sysenter?