Local Downlevel Document preventing printing

I have a user, who if he reboots his PC (for any reason), when he logs back in, and tries to print a document, two files will show up. The file he needs to print, and a "Local Downlevel Document" file. That LDD file will not print and locks up the queue until I remove the printer and then reinstall it. He is the only user in that entire department that happens too. We have tried blowing away his user profile and recreating it, removing the printer and reinstalling it, checked permissions, etc.

He is currently on Windows 10, 1803 ( I believe, yes its slightly out of date, getting updated later this week ), he was on a VM and then we moved him to a physical machine last week, and all of a sudden, he lost printing, and has been having this problem since. The error logs show no kind of printing problems even while that document is stuck. My boss and I are almost bashing our heads against the desk trying to figure this out, and any advice or help would be greatly appreciated.

EdTittel said:

Whoa! This Google Search shows lots of users with this problem, but no elegant solution. I'd recommend an in-place upgrade repair install on the user's PC. Won't take very long, and might help (or might not).
Weird!
--Ed--

Yes, many issues, zero solutions. I've been at this since 10am trying to solve this issue. Refreshing his PC is not quite a solution, i'm trying to get into his event viewer, so I can see if there are any printing errors.