The Remembrance Agent, remem, sounds really interesting.
I think the only way I'm ever going to get into Emacs is to immerse myself in it, use it for my shell, ftp client, news and mail reader (although I'll still need Outlook at work, but maybe I can copy all my email in plaintext to a repository which remem could access). Remem might convince me to do just this, as it's real power would be to bring all those things together.
One significant challenge is that this will be under Windows, running cygwin. I carry a Windows XP system, it only makes since that I'd try to make it work there.
I'll let you know how it goes.