plex media server not opening ubuntu 18.04

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I'd like to first secure the server as best as possible, make proper configurations, and then move on to building up the media server with the proper instances. So I guess my question is: where do I start? I know my way around the Terminal, but whenever I find myself unable to do something via command line I always just do it via the GUI. I must admit, however, that jumping into a fully headless Server OS has been a bit challenging as I have been woefully dependent on the GUI in Linux environments.

I already have a PLEX server running and am familiar with the software, but it is running on an old laptop using Ubuntu desktop with limited disk space. The idea would be to run a PLEX server, Sonarr instance, Radarr, etc, etc as this device would primarily be used to host and serve media content. I have decided to convert one of my old PCs into a home server and wanted to take the next step by running a full server OS (Ubuntu Server) as opposed to just flashing a regular desktop OS and using that as a 'server' like I have been doing.

Plex media server not opening ubuntu 18.04