Hi @Anthony thanks for the reply!
So I do see "drawing enabled" on. But it's only broken in that one project.
I started a new project with 2021 following all the same steps and it worked perfectly. So something strange is breaking it in my old 2021 project and I have to figure out what it is.
However, no worries I will keep researching to find the issue and if I solve it, I'll be sure to post what the problem was. I'm almost certain it is something I'm doing wrong.