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One of the easiest ways to "break" the DRM would be to write an app that automates the connect software and does window captures to bitmaps, then runs OCR on those. That wouldn't require any crypto smarts or reverse engineering, and any half-dencent Windows programmer could do it in a few hours (assuming they had some OCR software to use). Taking the firmware route (or attacking the desktop software) may result in a class break but its much harder to do, especially the firmware route (just contrast the number of people who can read x86 disassembly with symbolic debug info available for many of the DLLs with the number that can read ARM assembly).
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