2. Most PDF editing software allows you to add password protection to an existing pdf. (E.g. Adobe Standard ($450), PDF Converter Professional ($50-90)). Print it to a pdf, password protect it, then email it. Voila! Encrypted email!
An alternative program that I love to use is the
FREE PDF reDirect, which allows you to print anything to PDF format and set a password encryption to the file. I use this to combine progress notes and imported items into one large password-encrypted file when creating a disk of a patient's medical records.