I was able to implement this, but have another question. Here is my flow right now:
Loop through and create a multi-section report. Each report is a Table, using InsertTable because I don't know how many pages each will be. As I loop through I keep track of the page indexes at each section break and descriptions I have set for each section.
Once the entire report is written, I then insert a new page at position , draw a table with my table of contents, insert the Annotations as you have show above - and use the Block.Measure method to position the .rect in the right spot.
Finally I use the RadContentEditor's Position and DrawTable to insert my table of contents.
The potential problem is if my table is too long to fit on one page.... So now my question. If I create the table of contents in a separate RadFixedDocument so I can use InsertTable... Can I then insert the pages from that Document into the top of my first document? If so - how would I do that? If not - is there another way to accomplish this?