Is each number text but tagged as a figure? If so, you should be able to just pull the text out of the figure tag and put it directly in the label tag.
The numbers should be text but are not tagged at all (don't show up in the tags panel as a separate tag). What does show is as an LBody tag with "Image (123): w:16: h:18 The right to inspect. . ." instead of simply "1. The right to inspect. . .". in the container. When viewed using the Edit PDF tool they appear as an image separate from the text. They also appear as slightly lower resolution with distortion around the edges. I've converted documents from Word that use the same multilevel list tool with associated styles, including another one just today, and it didn't have this problem. The settings were the same in both instances.
Using the Edit PDF tool:
Also, it is only the level-one numbers that are doing this. The level two (a.) and level three (i.) numbers are registering as text.
Ah, OK. I do not have Word 2016 yet, so I can not duplicate or suggest a great solution. My work-around approach would be ...
Use the Touch Up Reading Order tool to tag each of the image-numbers as a <Figure>. Add Actual Text to each Figure tag to represent the number. Nest each Figure tag in a Label tag. You will end up with something like this ...
I couldn't test it either, but have you tried to create your PDF with the built-in Export of Microsoft Word?