So this reporting process is not automated, rather your workflow is being augmented by a user interface which tries to simplify the process for you. I would consider revising the question title to draw more relevance.
But it seems like that adds a level of complexity, where if there is very much nesting and looping in that part of the document, the user interface itself becomes more of a hassle than a benefit, making you have to do counting maths in your head to figure out which button you should click if you want to do a certain thing [create a child, or nested data point; create a sibling, or parallel data point, etc]. I can see how, with much nesting, it could get confusing fast.
Have you considered not using the RSCC system at all for this task, and manually creating the nested lists, using keyboard shortcuts such as 'tab' and 'shift+tab' to achieve the nested depths you desire?
I would say that if there are no proprietary or simplistic alternatives you can find, you could potentially create your own 'RSCC macro', using the Microsoft VBA developer console.
Macro development in VBA is probably not your forte (it's certainly not mine), but it could end up being a viable solution, depending on how modular the content control sections of your template are.
When you get to the nested parts of the document, click a button which runs your macro, which prompts you for the nested stuff, where you can use your own interface which makes the nesting/looping better or more straightforward for you, personally.
Seems to me though that creating the nested lists in the normal way is your best bet, because then you have the 'tab' and 'shift+tab' shortcuts to systematically nest and un-nest pieces of data from each other, in a context-aware fashion. (Meaning, if the current data point is 2-deep, and you press enter [to create a new sibling data point] and press shift + tab, it will know to move this new data point back, making it 1-deep, and now it is a sibling of it's previous sibling's parent. 904