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Cleanarr
Automatic cleaner tool for your mediaserver (eg. Plex). Making use of a history-tracker (eg. Tautulli) and a request-tracker (eg. Ombi) to keep in mind requested and watched status, to make sure media gets only deleted when everyone who wanted to watch it, has watched it. (by Cleanarr)
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InfluxDB
Power Real-Time Data Analytics at Scale. Get real-time insights from all types of time series data with InfluxDB. Ingest, query, and analyze billions of data points in real-time with unbounded cardinality.
Not really, If I want to watch something, maybe my friends do. I just don't want to give access to people who I do not know (for obvious reasons). Separating directories for each member seems like a very manual process, but if that's what you want to do, go for it. The only real benefit I could see about your process is the deleting of stuff, but then again, you could set up Cleanarr to do that for you anyways.