Very late to the party but my way of keeping track of what I've watched is via jellyfin itself. I use jellyseerr to keep track of what I want to watch. audiobookshelf for what I've read and listened to.
...keeping track of what I played or want to play is a personal holy grail of mine. Currently there's nothing that suits my needs.
All the time? I'm guessing you are talking about information that was lifesaving or something that is in your PKM, if so, then I can't think of a time off the top of my head but I stick to "all the time" because I really do use it as my digitized brain. It also revs my brain to come up with new ideas (yes I have a 'Ideas.md' file.
posteo is really cheap but a great service
My replay just shows how depressed I am.