[sneak]

Or just use ssh-agent, encrypt your key, and store everything per-file encrypted in Dropbox like everyone else does.

OSX Keychain stores wifi keys encrypted on disk with a key derived from your user account password.

The only passwords I need to remember are my for my GPG key, my ssh key, Dropbox, and 1Password. Oh, and my user account.

[jiggy2011]

I'd rather not use per file encryption with dropbox because that could break syncing in big files.

The idea would be to have everything auto-login when the drive is mounted and nothing auto-login when it is not.