As far as using Perl in newer versions of Windows, you shouldn't have any issues.

My personal preference for Perl on Windows is Strawberry Perl. And if you think you might want multiple versions of Perl installed, I'd recommend checking out berrybrew. However, if you're requiring support (i.e. more than relying on community support for an open source product) and are willing to pay for that support, ActiveState's ActivePerl along with their paid support might be better suited to your needs.