Following my suspicion of IIS, I logged in as the (Built-in) Administrator and used Server Manager to remove IIS and its dependencies completely, and then ran the installer again and now it works. Looking at the Server 2019 image I have (installed via WDS), it has IIS enabled by default, so IIS was corrupted from the start.
I am now able to log into the web ui without issue.
Thanks for your help diagnosing this, if someone finds this in the future, I hope it helps!