Operating System Woes

[TheDreadPirate]

...but I felt like every step I had to look up instructions or explanations for things I was already looking up to do.  I'm feeling a little overwhelmed but I've heard so many good things about stability and ease of use of Linux distros once things are all set.

This is the norm.  There is no one Youtube video or blog you can read to seamlessly transition your into Linux.  It will take time and effort.  And you will frequently have to research the steps to do things you took for granted in Windows.

Lucky for me I'm a professional Linux sysadmin so I was able to take what I learned early on at work and bring it home.

Dual booting, as you said, is probably the best option.  Or, if you have an old PC, RPi, or some other secondary device you don't use a lot, use that as your learning platform.

Regarding Jellyfin, if you're still having trouble getting it up and running, there is not a lot that needs to be done once the OS is installed.  I'd be happy to help you over in the troubleshooting sub-forum.