While both comments were invaluable, I think @IVNSTN's comment was closest to the case. I set this problem aside for a couple days to work on getting an API project running in my local environment. Since I had uninstalled VS during my troubleshooting, I had to reinstall it for the API project. (VS is not my team's IDE). After that was done I went back to my script and it was working as expected. I'm not sure what it fixed but I'll take it.