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If the others fall through, I’ll happily take it off your hands.

FileVault can be used to encrypt external drives, the trade-off is that you'll need to enter your password every time you plug it in. There's a decent guide on setting it up here

True, but that's only an issue if you haven't enabled FileVault and / or a firmware password - which you should be doing if you're letting other people near your machine!

The keychain does keep all of your passwords in one place, but they're all encrypted so even if someone managed to get through Apple's security, they'd still have to break the encryption on your passwords and, as of now, the encryption method they're using hasn't been broken. There's some more...