You might want to take a look at these example Pat, I spent quite a while with this some time ago, I found similar issues and found some solutions to the problems you raised. My example project was a simple Stockyard where I had the Base and then a Measured Surface of 3 piles, each pile had a boundary around it. I ran the Earthwork Report (Custom) using the 3 boundaries, and was able to generate the following reports as a result - I was using different templates to see what could be done with the Reports.
As you have found, the running of some reports creates a "Database of Results" and that database can be laid out in the Word Document using the Custom Report Editor in TBC. You can populate fields in the report using database elements (if you can identify the correct elements in the available fields). The fields can be embedded in lines of text or in Table fields etc of the Word document.
There are some advanced settings that I discovered that helps control multiple line entries and will suppress duplication of lines - I may have resolved some of your points (but it is a while back that I was doing this).
Feel free to take a look at the enclosed Templates and Report Outputs to see if there is anything here that can assist you.
I also enclose a Video that I recorded to capture the process. You can also find a TBC Power Hour that covers some of this but maybe not in the depth of detail that you need to solve your problem here.
Let me know how you get on - if you still have issues, please highlight the specific issues that you still have and I will see what I can get onto the development roadmap
Alan