(Un)fortunately I run perl on windows on a daily base, 2012 and 2016 too. I see no problem at all to switch (at least if no CGIs are involved in the migration.. ;). Me too I strongly suggest you to try Strawberry Perl. Look at their releases. I'd try directly the latest 64Bit portable edition (running the comfortable portableshell.bat tha comes with the portable release) to see if you can install GD and run your previously developped programs. With strawberry perl you can do the same as in Linux, just: cpan GD will suffice.

Then you can choose if install a "system perl" for the users that also modify the ENV

I also see that GD matrix is very green for windows users even with recent versions of Perl, so dont worry!

L*