I hope to eventually expand this into a section with screenshots and stuff, but right now I'm just trying to get the general skeleton done. Here's a quick rundown on how to do it:
Method 1: SSL
Tell your email program to use an SSL, or Secure connection.
Method 2: Forwarding over SSH
Tell your ssh program to forward local port 110 (for POP3) and/or port 143 (for IMAP) to remote host:port yip.org:110 or yip.org:143, respectively:
It should be noted that many ssh programs are buggy and will hold onto their forwarded ports after they are closed, forcing you to reboot before being able to use the forwarded ports again. Symptoms of this are either mail connections that just hang, or "Connection refused" errors. (Eudora gives error 10061, for example, I think)
Return to the Windows section.