Posting the script if anyone want to take a look and see if you find anything that stands out. Warning: it's long.
The error I provided in the original post is taking place in the "Water Full Grids" and "Pressure Zone Grids" sections. Both of these use the same grids, as well as the same layer files, though they are symbolized differently. Interestingly, "Water Quarter Grids" uses the exact same layer files as Water Full Grids, but it is at a smaller scale and there are way more maps exported (1800 vs. 490). All layer files use Maplex.
(I still wish DDP was more accessible in ArcObjects)
Thank you ahead of time for any and all suggestions 🙂