Rsync on a scheduled task is dead simple. If your friend can stomach WSL (Windows subsystem for Linux) being on the machine you might try using that. The command is a one liner:
For me: get enough sleep and/or do exercise. Getting 9 hours is my ideal but I settle for 7 more often than I should. As for exercise: running, hitting the heavy bag, jump rope, rowing, weight lifting, swimming, walking, VR boxing (got too sweaty for it to be a long term thing), rock climbing; all these things have been good over the years or whatever you want. Cortisol builds up in your system and exercise breaks it down. You can't be stressed if you're exhausted. I think of the two as shielding and loading. Sleep increases my shielding from stressors and exercise decreases my baseline stress load. The two together are the actual answer, in my opinion.
I invented a superhero called Molten Man who jizzes molten rock from his molten cock. I live in perpetual fear of Molten Man hiding above and/or behind me and getting hit by that spicy butter. Top, center, farthest back, in plain view of all exits.
My main bone to pick with Plex is that I believe that free and open source software should be gratis (free as in beer). You're right about the authentication though. I have mine set up with a simple user name and password over http. I rely on the VPN to limit access to the network through a forwarded port. I don't really like the idea of authentication being done on someone else's machine for privacy reasons, which is why I choose jellyfin that runs on my local machine. I'm not currently sharing it, and if I did I would change some of my security practices.
If you use Linux Mint, its a one click install from the software manager GUI and the config happens in a web browser. I use a VPN to connect and play videos from it on my phone. I like it and have it set up everywhere I can.
I have some videos I might be interested in sharing on a Jellyfin server, as well as interest in viewing videos on someone else's shared server. I have a question: What options do you have for hardening security-wise? I have the server hosted on a local machine and don't wanna get pwned if I can help it.
I have this exact use case too. I use Linux Mint with Jellyfin installed from the built in software hub. You cannot find it from the command line because it's a snap. The software app works and provides one click installation. Clicking on the jellyfin icon in your start menu brings up a browser tab that you can use to configure http access if you want. I use a raspberry pi running pihole and pivpn for a VPN and the wireguard app on my phone to connect to that VPN. This works on my cellphone over the network and allows me to access the jellyfin media via the jellyfin app. I think it works nicely. I have jellyfin media player on the laptops and the streaming works on the lan. I will caution that I haven't been able to easily set up wireguard on the laptops. I use phone to stream, so this might just be a motivation problem on my part.
Torrents are p2p and can be encrypted but aren't anonymous. Tribler claims to be tor-like and no trust needed i.e. anonymous.