My 10.11 migration blew up because one of my directories didn’t have enough space for the migration.

The path /var/lib/jellyfin/data has insufficient free space. Required: at least 2GB.

It looked like the jellyfin service started after the package install, but it was stuck in a loop attempting migration.

Burned optical media shelf life can be as little as 5 years, so I don’t think it should be recommended for long-term storage.

Easily defeated by those who play Minesweeper.

Any reason you avoided the official Raspberry Pi Imager software? You really can just configure a headless OS all before flashing the SD card. Choose RPi OS lite from the list, then set up your hostname, username, password, wireless and turn on SSH service. Then all you have to do after flashing is plug in power and SSH in. None of this display troubleshooting would be needed.

Two questions:

Do you have anything between the Pi and Display, like an HDMI switch? Sometimes the Pi incorrectly sets the display resolution if it can’t communicate with the display directly.

Did you use the Raspberry Pi Imager program? You can configure SSH and WiFi, before you even image to SD. It’s how I set up my headless stuff so I don’t have to futz with connecting displays.