Alternatively, if you want a project or want to learn more about Linux, going through a migration with software you already understand (Jellyfin in this case) is a good way to learn.

You should still reboot your Linux server regularly. While the updates can run in place, running processes will not pick up the changes until restarted. And when you update the kernel you also need to reboot the system to pick it up. While there are distributions out there that have systems in place to auto restart affected services and can upgrade kernels in place (e.g. Ubuntu with the right licence), it is still recommended to reboot every now and then. My server is set up to reboot once a month and after every kernel update.

I'm sure I could spend a day banging my head against google and mucking with my Docker containers to get it working, but I decided it's not really worth the effort.

You threw away a learning opportunity. I seriously doubt the problems you were experiencing had anything to do with Linux, specifically and were more likely due to your lack of knowledge about how Jellyfin works with streaming.

I'm not insinuating that you're a bad person or anything like that. Every one of us has limited time to fool around but it seems like a lot of people really do give up too easily on things like this 🤷

I've seen people spend hours and hours or even days troubleshooting (or just trying to work around) Windows issues/frustrations to the point where they say, "fuck it! I'm trying Linux!" Then they encounter one problem, spend ten minutes trying to figure it out and then just give up and switch back to Windows.

It's a trick or the mind: Human brains trust the familiar even if it's so much worse than something new. People get used to all the bullshit Windows throws their way and it becomes the new (accepted) normal.

It just seems normal to walk up to a PC that rebooted itself overnight and is forcing you to reopen and relogin to everything. It seems normal to instinctively close popups in the lower right corner of your screen without thinking about it because they appear so often. It seems normal that advertisements appear in strange places all over your computer. It seems normal that to install just about anything you have to search the Internet and download a .exe then run it with administrator privileges.

Windows enforces bad behavior and worst practices at every turn yet when faced with a new interface and new ways of doing (and troubleshooting) things users will suddenly find new problems infinitely more frustrating and unacceptable... Even if they're really just minor inconveniences.