Selfhosted
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It's curious that I'm almost in the opposite boat, have been using Jellyfin without issues for around 5 years, but recently was considering trying Plex because Jellyfin is becoming too slow on certain screens (probably because I have too much stuff, but it shouldn't be this slow).
Edit: this made me want to check in Plex, so I'll leave my story for people amusement:
My experience with Plex:
It's now been 1 hour of trying to set this up and I give up. Jellyfin is much more easy to setup, and even if Plex was instantaneous I could have loaded my TV library hundreds of times in the 1h I just wasted trying to get this to work. Probably every other time I tried I got similar results which is why I have an account there even though I don't remember ever using Plex.
Edit2: after some nore more fiddling managed to get it working, not sure what I changed, so now:
The quality was probably bad because you were routed through Plex Relay services which have a bandwidth limit. It is honestly quite a nice free service because it means it will work pretty much regardless how your network is setup but the quality will be bad. If you want to directly connect to your server you need a public IP so CGNAT won't do you might also have to open some ports.
Even though they're both on the same LAN? That sounds stupid, why would I need my videos to travel half across the globe to go from one room to the next?
You should not be using NAT to access your Plex externally, I will explain.
App.plex.tv and the apps use Plex services to generate a point to point connection from remote clients through your router to the server. This is important because you never need to expose a private IP to the Internet, and the authentication can be protected with something robust like a Google account which support 2FA and even phishing-resistant 2FA.
The combination of more advanced security and secure/convenient SSO authentication are one of the biggest benefits of Plex in my opinion.
This is more about familiarity than difference in ease of use. I've used both, they are both super easy.
Some of it yes, the claim for example, but the rest is still pretty bad UX (and even that is stupid, I shouldn't need a claim to watch locally), I'm an experienced self hosing person and I'm getting frustrated every step of the way, imagine someone who doesn't know their way around docker or is not familiar with stuff... Jellyfin might be less polished as some claim, but setting it up is a breeze, never had to look at documentation to do it.
I set Plex up as an inexperienced selfhoster in 2020 and it was easy.