Looking at it closer today,
I looked at the File Manager workflow and it was giving me the error
04/22/2019 10:33:06 AM jsxCallWorkflows Skipping '20190421_061502-INCREMENTAL-transaction_lines-000000_0.gz' because a file for this feed is currently being processed.
I was able to find in the FileMapping/File History that there is a file that is stuck in "In process" status from 10/16/2018.
This makes sense as to why the File Manager JS is telling me the most recent file is being skipped since there is another file stuck in the process. And also why the Data loading activity kept erroring out because the file provider was not providing a file to it in the JS.
Any idea on how to unstick that file?