Extend OutLook Add-On

I have a current OutLook Add-On module that uses the COM Shim and a VB.Net 2005 component to perform several functions. It connects to a web-service on our servers to sync contacts. I am looking to add some additional functionalty to this add-on. Specifically, the following. 1. Add a new "right click" menu item on a given contact called "Track correspondence". When selected, it will store a piece of data for that contact that can be used to determin whether to invoke a web-service call upon sending/recieving emails. 2. It will connect to an updated web-service API, which will have a SaveMessage() method, the saveMessage will take a message object that has the from, to, subject, and email body text. 3. Add a new even for sending/receiving email. Upon sending/receiving email, the system will lookup the contact via the email address and then determine if the "track correspondence" flag is set. If yes, it will call the web-service method passing the contents of the email message. This event will be registered for both sending and receiving email.