Why not take the touchpad metaphor all the way? Have a separate button for clicking. Your other hand isn't doing anything but holding the device. Have an intuitively placed button for that hand used for clicking. One hand moves the cursor, always in contact with the touchpad, the other clicks. Or if you do want multi-touch with both index fingers and two cursors, provide thumb buttons for clicking. Seems pretty straightforward, and likely a lot less complicated than this fake-finger-shadow business.

Because he loves to do things he hates. Masochism at its finest.