I have been using Obsidian for a long time. Started using it at the end of my time in school and now it is my "second brain" as they say. I have a sync sub and they way they handle it is fantastic. They email a week before the sub is due (I have a yearly plan) to remind you it is coming. I have 3 different vaults to keep a few things compartmentalized. And I just got my own sync server set up locally with the community-made live sync, which so far has been better than Obsidian Sync. I love that even if they took the program to a subscription model I would be able to keep my files with out having to convert them or export them.
I always get weird looks when I am shopping for appliances and I ask if it is smart. The rep gets all excited and starts talking about it. I say I don't want a smart one. They look like I am from off world.
This is were I would like to move. But not really a good option. I have a Linux tablet, desktop, and server but no phone hardware yet that is good for daily use.
Jellyfin I don't have to update if I don't want to. Jellyfin can't force me to update by taking a function I currently have away or force my to pay to keep using it the way I currently am. With open code I can fork it and keep it at the version I want if I choose.
I am curious as to why people thing Plex is self hosting if Plex can change how your server functions? I have never personally considered it self hosting but do others still think it is?
I look at it this way, if I made a copy of this work irl would the person who made it go without their needs met? If I bought it IRL already then it is always fine IMO. If it is a independent person I try to buy it in a way that they get most or all the money and I get files that are not DRM. It really a case by case thing. Like I will never give Nintendo or Disney any money ever again so I have to find ways to get what I want most of the time it is second hand or pirating it.
I would see what you could vibe code or just check if Linux can just do the automation your looking for built in. It depends on the desktop environment but I know KDE is very powerful if you are willing to put in the time.
This is kind of the best way, the wife vpns to there to watch lots of it because the us one sucks.