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Originally Posted by BoldlyDubious
For both reasons, I see as pretty unlikely that this kind of people will turn into expert hackers and will turn to doing something clearly criminal such as breaking into other people's PCs and stealing files.
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A more likely scenario is this: Mary uses a computer but isn't technically inclined when it comes to fixing issues with it. When she has a problem, she has her grandson John or her nephew Bill fix it. Or that nice boy Andy that lives next door who's good with computers. After all, he was probably the one who helped her with her new gadget in the first place. Suddenly Mary's watermarked ebook collection is on the internet.
I used to do tech support in a retirement community. I lived in that community for over a year. The DRM scheme you propose brings this very scenario to mind every time I think about it.