Hello Shawn,
SpanBoxPositionHandler is used with document positions, which are mainly used to navigate through the document like when you use the arrows on the keyboard or change the caret position. You can read more about document positions here, but I don't see in what way they would be helpful in your case.
As it comes to the DocumentElementCollection and DocumentStructureCollection, they implement the logic that would allow adding document elements (such as Paragraphs and Spans) to the Children's property (Blocks or Inlines) of the document element that can contain them. You can get a picture of RadDocuments's structure in our online help.
If I understand your scenario right, you know where you wish each list item to appear and what number it should be assigned. In that case you can insert it like this:
And then add these paragraphs to the document like this:
Let us know how we can help you further.
All the best,
Iva
the Telerik team
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