OP — Plex is a step easier, as Plex brokers the connection. No reverse proxy. The same plus in this case can also be seen as a minus.
I’m still on the Plex bus, and it’s good for me and friends. Jellyfin will get there one day, but right now it’s just not quite feature complete enough for my use cases.
Irrelevant, unless your pihole is running on your DHCP server. Does the server running pihole have a statically assigned IP that is within the DHCP range being assigned to other devices?
Static addresses should be outside of your DHCP range, ideally. If you can’t change the range, and assuming sequential handouts of IPs from your router among other things, you can try setting the server’s static IP to a bigger number.
I’ve just started a Zulip POC and it’s been decent so far. Definitely resembles Discord.