I started working on easy-to-follow, baby-step approach tutorials on how to use encryption on Windows. My motivation is to teach my wife how to install and use GnuPG and eventually OTR and TrueCrypt. So far, I've completed the GnuPG How-To. Hopefully someone else is able to find it useful.
I decided to write on how to secure a Windows install with a few freely available programs: Eraser, TrueCrypt and Core Force.