So, I tried to run MicroPython and it starts and executes simple commands well. Next step is running the testsuite, and that's where I hit the problems. Testsuite requires CPython (to compare results against), and the latest versions of CPython for Windows are distributed as MSI archive. But Windows for IoT doesn't have "msiexec" tool to install it. I tried to install it via generic redistributable package offered by Microsoft, but that didn't really work. Generally, it seems that any GUI applications don't work on Windows for IoT - it's essentially a headless version of Windows (you work with it accessing command line via telnet).
All the above didn't really stop me, and I installed CPython from MSI on my Linux box in Wine, verified it starts, them carefully copied all its files and (hopefully) all dependent DLLs to Galileo. No avail - CPython doesn't run (no errors, just running command exits immediately). More info may be available to my post to python-dev: https://mail.python.org/pipermail/pytho ... 37234.html
Bottom line? MicroPython already support Windows for IoT better than CPython

I hope to update this topic from time to time with more news/results.