LOng term certs (x509s) would be great. I'm looking/wanting to do
like an old style "kings" ring stamp electronically so I don't
have to fill out all the BS.

I really don't know if its possible. I have seen some password
"generators" that have like a master key and create subkeys based
on website. Most of them that I have seen are java based, and java
  "leaks" information so I wouldn't trust it as far as I can throw it.

I already manually have my "bands" of passphrases that are used
depending on what they are being used for at the time. OTR is
cool, and I have used tokens at work before. I'm becoming more
mobile and I can guarantee the security on my boxen but not
necessarily the network I am on. So I have had to find "secure"
methods of communication at least until it reaches another server
out of my direct IP zone. This in turn would mean that whats
coming to me once it hits certain servers is coming into me
secure. I recently sat in my house and turned on wireshark to see
what was in the air around here. It's pretty enlightening to say
the least.

Oh the wonders of trying to keep yourself "free" from those that
want your personal data for their use.

Vi^3PP

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