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There are two ways to do it - I just did the quick and easy way and have both of them on my account, so it's a snap to share books. When I buy a book from Amazon, I pick which Kindle (Beanie or Cecil) it's sent directly to. Both Kindles access the same Amazon library (via Content Manager), so even if I send the book to one Kindle, the other can access it. The advantage of that is when your reading doesn't overlap with the other person - there are a lot of books I read that he's not interested and v.v. (the "economics doomer porn" kills me), and when I buy a book it isn't automatically downloaded to his Kindle. Multiple Kindles don't have to be registered to the same person to share the Amazon library, though, but you need to go through Amazon to get your devices linked. I have a friend who is buying one just because he's used to borrowing books from me, so I'll have to get his linked in.
Magazine and newspaper subscriptions are only for one Kindle though, so you have to pick who gets to read The Atlantic and who gets The Nation (that one was easy).
Non-Amazon books can either be emailed or mailed through the Kindle system. I haven't tried the email thing, but supposedly there is both a free way and a 0.10 fee way (I'd guess that one uses [yourKindlenameID]@kindle.com and the other one involves using [yourkindlenameID]@freekindle.com).
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