Hello,
my experience: as a new Jazz user (crossstar 2025), first thing I tried was to update what I could (maps and system sw ).
I had the same message as per your 1st screenshot; I am using a mobile phone (android) in hotspot mode to get the data.
I declined the update with engine off, and did it on the spot. What happened next is:
1. It took some time to do the update (I thought it would be faster)
2. It confirmed the update was completed and it rebooted. Reboot was also rather slow
3. Upon startup, the navigation apps, embedded garmin and the android auto would not start (garmin would refuse to start, android would be unable to accept any route

) . Radio FM/Dab and other apps ok though.
4. To recover, I had to reset the system (option under 'Systems' menu). This also was rather time consuming
4.1 Upon restart, I had lost my personalization (radio stations, saved places in garmin, etc), so I had to reenter these; on the positive, it seems the system did update

Bye, bye
Giovanni