This link may help with disabling SSL for you. This is necessary because the PGP proxy needs to receive the email as plaintext to be able to encrypt it. If you have the email client encrypting it first with SSL, this is not possible. However, if you disable it in your email client (Outlook in your case), PGP will make the SSL connection with your server after it acts on the email.
I don't know that there is a way to directly shred Outlook email. However, on the Disk tab of PGP Options, you can set PGP for shredding files when emptying the recycle bin. If you make this selection, all files, including all system and application temp files, will be shreded when they are deleted. Files that first go to the recycle bin (a lot of files such as application temp files skip this) will not be shredded until you actually empty the recycle bin.