Thanks for the advice gentlemen. I think I may have finally got it working. I ended up starting over and deleting my "Connection Request Policy" and "Network Policy" from MS NPS and started over following
this guide which kept everything very brief.
It also seems strange that I had to tie to policy to a certificate for the server itself. Not the certificate that shows as the root cert for the computer certificate (which was generated by force of a group policy). Absolutely nuts.
I am going to go back over this tomorrow and ensure that this is working as intended, and maybe write up some instructions on how to set this up from end to end.
And thanks for those docs you sent me Ron, those were quite useful!