That is not correct. The Plex Pass is for your account. If it was for your server, you’d lose your Plex Pass if your server ever died and you had to recreate it. And if you had more than 1 server, you would need another Plex Pass.
There are Plex Pass features that your server can then utilize and there are features that your account can utilize. Plex allows some of these benefits to extend to managed users or to other users you share your server with. It is not a blanket “shard users inherit all Plex Pass features”.
Sleep Timer is a new feature and currently limited to a Plex Pass account. Managed users do inherit this ability. This may change in the future but that’s the way it is as of now.
Not an easy way. You’d have to manually edit the Plex database. There was an older discussion on this topic. Not sure if it still works. Copy a Managed User's Watch History
