Wow, going through that was a bit emotional. You've got to set up an email that gets sent to your contacts when you've been inactive for >3months. That'll only happen if I'm dead or imprisoned so, yuck. Did not enjoy typing that one up.

Yea, I got to that step and closed out. I need to set aside some time this weekend and think about what to write.

Wow, what a frighteningly effective deadman switch. Normally I'd be worried about forgetting to reset it but in this case it's hard /not/ to use a Google product in a normal day.

That's a fantastic hidden feature - thanks for pointing it out.

Is it safe to put my 1Password's master-password into the message that is sent in case I'm dead?

How about the name of the book on your parents'/friend's bookshelf with your password lists in? Or some clue to a more secure hiding place.

I'd say no. I find an offline alternative to this.

The ability to attach files to the autorespond email is unfortunately arguable both for and against.

If at least one of your friends is technically minded you could probably use yEnc.

My security-mindset-sense is tingling..

Could be an attack vector when you know someone's google usage will be sparse.