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A more eye-opening challenge would be: no free-open source software for a month, no services using open source software (no sites running on an open source OS or server etc.) and no operating systems which are even partly open source (so no OSX either).

Another less radical but still quite interesting variant would allow using open source licensed software (BSD, Apache etc.) but no free software (GPL, LGPL etc.).

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I'm not sure if it's still true for Windows 7, but I remember that XP also used some BSD code in the network stack. The challenge shouldn't really be eye opening. Free working code will make its way into many pieces of software.

Your second challenge is more interesting, as it may illustrate the effect of using more restrictive copyleft licensing in terms of code reuse.

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