2. Encrypt files on the Dropbox server, in a "transparent" way, so that I do not need to use passwords to sync between org and Iphone (which I let Emacs do automatically once each day).
This is what MobileOrg's encryption is for. You set a password in your .emacs and then the same one on MobileOrg and the files in dropbox/webdav are encrypted, and there is no hassle. Note that MobileOrg only has encrypttion support in the beta 1.5, not the released 1.4 - I have a beta and am using it/testing it.
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