I don’t mean to add fuel to the fire with Gentry or anything but I can speak towards my experience with jellyfin here. When I started with jellyfin I didn’t know a lot about networking or even self hosting, I pretty much jumped in blind. Although it’s fair to say I am not new to technical concepts/troubleshooting so my experience is definitely going to be smoother than a non technical user.
For context I am using truenas scale to host jellyfin and I was able to install it, configure it, and get my library going on the first try and it was definitely under 20 minutes. Once I decided I wanted remote access to my library it wasn’t super crazy to figure out tail scale (maybe 30 minutes?) and have that available too. It might not have been under an hour total but coming from almost nothing as a newer user I didn’t really experience a lot of turbulence.
I currently dual boot like this. I’m still really new to Linux but I always wondered about this meme since I didn’t have to change my boot settings other than to boot the drive with Linux first. Now it makes sense but it had me wondering for a while there!