Read: FAQ 27 - Migrating an existing PMS from DSM 6 to DSM 7
Read: Installation & Setup of Plex Media Server on Synology
Before updating to DSM 7:
a) Uninstall Plex Media Server
b) Do not delete the Plex shared folder, which hold metadata, the database, etc.
After updating to DSM 7
a) Synology Control Panel → Security → Logout Timer = 65535.
Installing Plex may exceed the default value. You can change it back to a realistic value after the installation is complete.
b) Install Plex Media Server.
Pay close attention to the messages regarding file permissions, as mentioned in FAQ 27 and Installation & Setup documents.
As mentioned in the FAQ, depending on the amount of media, it may take some time to migrate to the new version of Plex Media Server (1 minute per 1000 items). Let the installation run. Do not interrupt it.
If the migration is successful, the information in /Plex will be moved to /PlexMediaServer, and a migration log file will be in /Plex.