Hi Drew Reutlinger,
Generic Content is RadEditor wrapper. Inside the Generic Content control you have just HTML. You can achieve your goal by creating a custom control that inherits from Generic Content and implement a custom designer for it. You will find a sample code here How to wrap a Generic Content control in 3.6 SP1
Inside the designer there is a method - OnSaving() - called by the ControlEditor when the component is about to be saved. You need to override this method and you should not call the base. You have to get the content and check for dynamic links. Then resolve the link and get the content item. Afterwords you have to get the mime type of the item and alter the HTML by adding an image using RegularExpression.
// this is the RadEditor content which contains all dynamic links.
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