in reply to Two operating systems.
I wrote an article about doing something similar with Perl and VMWare (which has a Perl API) to build a test farm for the Krang project. Check it out here, might give you some ideas:
http://www.ddj.com/web-development/184416172
Another option to consider is Wine - you could potentially run your Windows program in an emulated environment. I've seen that work successfully to run a Windows-only geo-coder under Linux.
-sam
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