Key management is pretty primitive. It would be nice if SSH integrated better with PGP/GPG. I recently spent too much time messing with monkeysphere, keychain, gpg-agent, gpgsm etc. trying to use GPG derived keys for SSH. While I could cobble something together I didn't feel that it was a solution I could recommend to others as a general "best practice" because it involved too much installing and configuring and was still somewhat brittle (eg. providing key names to gpg-agent in my .bashrc file).