A lot of the documents we make at my work follow the same format; the document that takes the most time is, without getting into too many details, a report on a project that a client undertook. The report details the name of the project, the names/contact info of the people that oversaw it, and information on the project itself (like how the project went from initial design to completion).

Because all of these reports follow the same format, they all have snippets of identical information (boilerplate bits). However, some projects are more involved than others, and have more twists and turns in their design stages. I've drafted a template in MS Word that automatically fills in the boilerplate bits, and has content control sections for the things that need changed by whomever fills in the document.

However, one of the sections has nested bits that, potentially, could repeat forever. To spell it out, the document details an item that was made during a project, how the item was originally planned to have worked, what didn't work about those original plans, and how each of those issues were overcome.

As simply as I can see it, there are 3 levels of this list. Say, for example, the report was about an alarm clock company trying to make a bigger alarm clock:

We wanted to make an alarm clock that was 50x the normal size

This alarm clock would not fit on a regular table

We made a table that's 50x larger than normal, which the alarm clock fit on.

But what if the company wanted to make a bigger alarm clock, AND they wanted to make a waterproof alarm clock? And what if they tried multiple things to fix their issues? So, each level of this list needs to be able to repeat independently to make lists like this:

We wanted to make an alarm clock 50x bigger than normal

This alarm clock would not fit on a table

We made a table 50x bigger than normal, which the alarm clock fit on.

This alarm clock died quickly with AA batteries

We connected it to a generator, which powered the alarm clock without issue.

We wanted to make an alarm clock that works underwater, by putting it in a box

The box didn't keep any water out

We made the box twice as thick, which still didn't keep any water out.
We made the box out of metal instead of cardboard, which worked.

And so on. Now, this can be done in Word 2016 using the "repeating section content control" (RSCC) by nesting 3 together. However, the way an RSCC looks for a user, there's a button that comes up in the bottom-right-hand corner of the section-to-repeat. This is fine if what you're doing is repeating a single row of a table. But when you get to 3 nested RSCCs, You have three buttons right on top of each other, which gets confusing and ugly.

Is there an easier way to make a multi-level list's sections independently repeat aside from using RSCCs? Would there be a better program to do this in? From what I can tell, there isn't a way to do this in Adobe Acrobat XI.

Am I going about this the wrong way? Ideally, I suppose a process could be drafted in a couple of paragraphs. Because of the nature of these reports, however, it is more efficient to explicitly list the project idea, the problems that those projects had, and the way these issues were resolved.

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