Writing and distributing DRM-removal software might be legal in Canada today, but it may not be forever if a DMCA-like law gets passed. Also. you would be at risk of prosecution any time you visited (or passed through) the US.
The only approaches that make sense are the effectively anonymous stand alone DRM-stripping tools and 3rd-party (anonymous) plugins. Note that plugin interfaces need to be for more than DRM-removal.
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