Wanted to finally update this. Remember this error:
Waiting for Internet connection to update pkg metada and finish package reinstallationUpdating pfSense-core repository catalogue…
Essentially, it was FreeRadius. It needed to be re-installed but, with the previous problems I was having, it was not working. Once I resolved those (i.e. Internet and Internet VPN working), I was able to reinstall this package. That took care of this.
Hopefully, this helps someone dealing with the same/similar situation.