Here are the most useful resources that I've found so far ...
Plugin Tutorial - Adding a custom action to Confluence This shows how to add an action to the "Tools" menu that appears at the top of a confluence page. Additionally it shows how to interact with the Page object to get more info about the page.
Plugin Module Types - The second guide I found helpful was the list of general plugin module types. It was informative to discover that a "plugin" is really a collection of "modules" and seeing this list was helpful to understand how to apply that model to creating a plugin of the type I was looking for. Additionally the Confluence Plugin Guide was also helpful for a breakdown on Confluence specific plugin modules.
The Confluence Developer FAQ Was useful for information on how to convert wiki content from a page into HTML as well as a number of other hard-to-find gems.
Finally, it was hard to find, but in order to understand how to "target" a particular menu or area of the existing UI to extend, I found it very helpful to read about the guide for Creating your Plugin Descriptor.