Instead of minutia, I’m just going to mention the few reasons that really sold me on containers.
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Security: Being able to host external services that only have access to the folders I map to it.
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Compartmentalization: I can specify exactly what resources I want to limit/control for each individual service. I.E. stacking a VPN on top of services for a 100% guaranteed Killswitch.
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Automation: Docker is an incredible tool for automatically restarting services whenever they hit a snag and keeping your services up to date with the latest version.
You’re not doing anything wrong, the playlist function is just half-baked. My guess is they put just enough work into it to intend for it to be used in small chunks, such as a single evening.
Edit: I’ve just seen your clarifying statement, and although Plex playlist is relatively non functional I’ve never seen that specific behavior. Try hitting play on an item in the playlist instead, that works for me.