I can only really speak to your first point. When imported my existing library, I did it using Sonarr/Radarr as applicable. They have a manual import method, here's a description of Sonarr's.

Unfortunately that'll probably work best if they're formatted in a way Sonarr can readily recognize, something like /Season ##/S##E## - .ext. It may take a little work to get there, I found a program called mmv which helps out a lot. It allows you to move files that match a pattern, capture parts of pattern, and use that captured part to name the output file. That allowed me for format entire seasons at a time, but that method does rely on most files having similar names to begin with.

Since Jellyfin v10.6.0, it's had a feature called SyncPlay allowing multiple users to watch the same thing at the same time (coordinates pauses, fast forwarding/rewinding, and all that between clients). I've used it and it worked like a charm, although I did find that not all clients support it.

I doubt Reddit builds a decent search engine, that doesn't actually help them at all.
If users can search, they find a previous post pertaining to what they want to see/know and they move on.
If there's no search, users can't find old posts or comments so they make new posts about a previously posted topic and more comments are made as other users react. That's more content, even if low quality from a user perspective, that shows engagement which can be sold to advertisers.

That's before considering the engineering effort it takes to make a good search engine, constantly fine tune that algorithm, and try to outpace those that are trying to game the search algorithm.

Sunday afternoon, after careful evaluation of a significant security concern, we made the intentional decision to sever our ties to the internet.

I feel like most big announcements like this end up being Ransomware. Cutting off from the wider internet feels like a weird move to defend/mitigate that? Unless it's to reduce exfiltration?

Gfycat is shutting down and deleting their content on September 1st.

I assume you mean SSL/TLS certificates for internet accessable applications? I use a reverse proxy called Caddy in a Docker container, which handles requests from the internet and directs them to the proper docker container based on the subdomain. It also handles my certificates automatically, requesting a new Let'sEncrypt cert just before the old one expires using a community made plugin.

You may be able to use the CLI tool mmv, which can be installed through the apt package manager. It's great at renaming files that are starting a similar naming convention and ending with a similar naming convention, you could use mmv to move your files. It also suppose sum links and hardlinks. It's what I used to rename folders of tv shows when I need to do that.

It's all about what you value, and supporting the things you love (or rely on, in a more utility sense). I'd value the speed, the lack of data collection that may be used against a user, the speed, the location options, and that same provider being in business for time to come. When I'd need a good VPN, nothing else will do. That seems worth the couple of USD per month to me, whether that VPN is for obscuring traffic I don't want others to know about (whether it'd be because of those facilitating the connection or the other end of the connection).

I hope so too. But he's already not supposed to be using Mar-a-lago as a permanent residence. So we'll see what happens.

I doubt even for health reasons, probably more for security reasons. Secret Service securing a prison would be a nightmare for anything short of splitary confinement. For that reason alone, he'd probably be under house arrest.

I use a fork of OpenBoard with Swipe Typing libraries added to it.

https://www.theverge.com/2023/6/16/23763661/reddit-rif-is-fun-developer-ceo-steve-huffman

RIF developer pushing back on Huffman's claims that RIF didn't want to work with Reddit by releasing emails.