I'm pretty curious about the initial break-in on his .mac account. I suspect that either he's misremembering and he has used the password elsewhere (and it was compromised there -- easy to happen over so many years of use), or it wasn't very strong to begin with and it got guessed after a handful of attempts.
There are a handful of takeaways from this:
- Backups, obviously. A lot of people here so far are mentioning online backup services, but those would be just as vulnerable to this kind of attack, since they're accessible online and use an email account for password resets. Online backup services and physical offline backups solve different problems and it's a good idea to use both.
- Since I haven't seen this mentioned anywhere else: I wonder if it's time to consider keeping a "secret" email account that's only used as the password-reset account for all of your services? Something that you never use for communication, never publish anywhere, something with its own entirely separate password.
- Be careful about owning multiple devices from a single vendor that provides remote access and other kinds of control to those devices. Mobile devices are inherently insecure; they shouldn't carry sensitive personal information, ever. There are a lot of really good reasons for going with a single vendor, and remote wipe is a really valuable tool in case of theft, but the downside is ... well, this.
- Use some kind of password storage mechanism. (I prefer something that's not tied in to a publicly-accessible service.) I've made a game out of memorizing horrible passwords, and can recall quite a few without any patterns or mnemonics or the like. Still, I use KeePass every day anyway.
And maybe most of all: I doubt there's a single one of us that has a moral high horse to ride on this. Everybody always has something better to do than set up a new backup system or dick around with something that will only maybe hurt them someday. I'm constantly harping on other people about backups, but only a couple of days ago got my development machine on our network backup system; I'm pretty anal about passwords, but still I'll panic pretty badly if my laptop is ever stolen, because in there, somewhere, is probably a plain text password stored in a file that I've forgotten about, and there'll be a chance that I'll forget to change that particular password if I find myself having to suddenly change every single password for everything I've got access to.