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The problem would be breach of copyright. Thankfully, there are some companies that allow you to use 2 copies of things, like software...Office, for example, gives you legal rights to use it on both your home computer and your laptop. But even music legally can't be used in two forms at the same time. For example...if you have your CDs in mp3 format, you legally shouldn't have them on your computer and on another device--even if you own the actual CD. And if you play the CD (i.e. it doesn't serve as solely an archive), then you're also breaking the law with an mp3 recording on your computer.
It's very similar to the wi-fi argument...it's clearly breaking the law, but the chance that anyone is actually going to enforce that law is unlikely.
The other problem with the scanning idea is that it is a HUGE investment of time. By the time you scanned and edited your book to bring with you on your PPC, you could probably read the book in its original format (and probably would while editing).
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