It’s may be a bit strange that the error changes after a reboot, but
ConflictInMappingEntry may indicate that you have this:
Or maybe more likely because you have a modem and a router:
The new error when checking for update may or may not mean anything. Possibly just a temporary issue on the Roon server, for instance. They released an update earlier today. I would wait for a day to see if it goes away before I’d start worrying about this.
EDIT: Just saw someone else with a similar update error when trying to install, so I guess it’s really just a general issue on Roon’s update server