Both Python and Windows work equally well regardless of the OS. In fact, I code in both languages on both Unix and Windows, and even use the same IDE cross-platform and in many cases, cross-language.

About the jack of all trades comment... I'm a jack of all trades in both languages, but I've also written some extremely complex and significantly focused applications and suites using both Perl and Python. In reality, it was Perl that allowed me to become such a good jack of all trades. That skill just transferred over to other languages nicely.