(...) make and test this on my linux machine what kind of headache am I looking at to deploy it on the windows machines at work. They'll be running Strawberry Perl.
If you write Perl and do not rely on OS specific external programmes and oddities, chances are very good that it will run on Windows and Linuxes without quirks or changes in the code.
However, if your choice was to use OS specific features the special variable ^$O yields the name of the OS and helps with that, too.
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Others making s'mores by the fire in the courtyard of the Monastery:
(5)As of 2017-01-25 00:10 GMT