Not really the best metaphor, as in Monopoly you actually start with money. A better analogy would probably be something like:
Imagine you're playing Monopoly, but you don't have any starting money and all the properties are already bought up. Every time you pass go and collect $200, $180 of it immediately goes to the rich. That is how most people live their lives.
It's nice seeing how much Lemmy is growing. I knew there would be an influx of new users from the 30th, but it's honestly nice seeing more comments overall and posts getting upvoted.
My understanding is that using Plex/Jellyfin is perfectly fine. The only real concern would be the actual way that the media was obtained, but you can host whatever you want on Plex.