What they said.

Upgrade as fast as possible to as current as possible. I convinced folks at my $job to upgrade Perl, but we've been so slow at it (priorities I don't control) that the one we're still planning on upgrading to is already out of date (not Perl's fault, it's on us). (The next version up for us breaks too much existing old code base.)

I don't know Windows well, but is there something like Brew to help with managing different versions of Perl on the same box? Or skip Brew and just be precise in the shebang.