What would be the easiest/quickest way to get somebody who isn't computer-literate set up to have the ability to transfer money to me via Bitcoin? Also, Bitcoin touts that it is anonymous. Is it any more anonymous or untraceable than a simple cash transaction?
The easiest way would be to create an online wallet on blockchain.info, and use one of the easy deposit features it offers. This however is impractical both for traceability (his, not yours), and for fees (which might even be higher than the taxes AFAIK).
That said, bear in mind that usually you might convince people to use bitcoins when they have something to gain, not when you do: consider carefully why should they do it before asking them to.
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