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I had a similar requirement in last project.
We needed to create contract documents templates with a Table of Content, like this:
The Contract Document Template had sections and clauses pre defined, but users could remove or add clauses if need, and ToC need to update automatically.
What we did was create a blank Word Document just whit a ToC, then we included it as the only clause of a first section called Table of Content.
All Contract Documents Templates had this as first section.
In Template file of Contract Document Template we also included a file that define which Headings (Heading 1, Heading 2, etc..) should be used for ToC. We needed to include this in Template file the one that sets margins and default fonts, it not work if you set this in the ToC clause document directly.
As results the document is generated and users just need to click right button in ToC and update it.
That was not an issue, because some manual steps were always need in document, and that could change pages of each section anyway. But, fonts and which Heading need to be considered was a great benefit.
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