All the official methods used to verify updates share something - they don't work as expected. What you describe is common. And it has been like that since 2017, when the old french MyPeugeot personal page (https://mypeugeot.peugeot.fr/) was used to verify updates, then the MyPeugeot App (MYPEUGEOT APP - Apps on Google Play for Android or MYPEUGEOT APP for iPhone), the Peugeot site - PEUGEOT Navigation Map Updates | Peugeot UK and now the Peugeot Update software (https://www.peugeot.fr/majesticinstaller/peugeot_update.exe for Windows or https://www.peugeot.fr/majesticinstaller/peugeot_update.dmg for macOS).I'm not sure why the MyPeugeot site didn't tell me there was a new map when I entered my VIN - perhaps it only knows what I have via the Android app - which only seems to work intermittently!!
No, the licence is specific for the infotainment system serial number AND firmware update version, so you need a different one for each new update. But as Mr Lee wrote, you might not need the licence file in the flash drive.I tried to use the firmware file but without the licence it doesn't work. I have a licence file from last December but I don't know if that would work.