Coincidently, i've been thinking about creating a pet web project to solve #1 utilising PGP.

The general idea is that you (the user, manually or through a client) locally PGP encrypt the text with the public PGP keys of the friends or family whom you'd like to receive the text by e-mail. The encrypted text is then sent/uploaded to the webapp. If you don't report back after X amount of time, the web service sends the text by e-mail to the selected friends or family. The webapp would not have any private keys therefore no access to the unencrypted text.

Not sure if there's already a similar service.