update: sudo profiles renew -type enrollment just immediately brings up the prompt again and it still fails to install over the currently installed MDM profile.

@strayer Are you able to remove the user-approved MDM profile, and then do the "sudo profiles renew -type enrollment" ?

@txhaflaire that worked, it ended up being a little more involved. Posting my full steps here in case someone else runs into this:
Remove MDM profile via Jamf

Sudo Jamf removeFramework

verify all profiles are gone. Remove profiles that aren’t.

sudo profiles renew -type enrollment

Have user approve the profile

Received error: The mdm server for your organization returned an unexpected status 403

delete the /Library/keychains/apsd.keychain file https://www.jamf.com/jamf-nation/discussions/29413/device-enrollment-installation-failed-the-mdm-server-for-your-organization-returned-an-unexpected-status-403

Actually needed to reboot into safe mode (by holding shift at boot) due to terminal and other apps crashing.

sudo profiles renew -type enrollment

Approved profile, and Jamf start pushing other computer profiles down.

Rebooted back into normal mode and the apps that were crashing were to be working normally.

@strayer Are you on Jamf Pro 10.15.0 or higher? It looks like the issue that requires you to delete the apsd.keychain file was solved with this release.

https://www.jamf.com/jamf-nation/feature-requests/8525/when-device-certificates-signed-apple-iphone-device-ca-are-evaluated-their-validity-dates-should-be-ignored