Thanks for the replies. I actually made some headway. 

On my Chromebook - 4gb Ram / 32gb SSD (Soldered to the board) - I was able to install Pop! Os last night. Checking it out for a couch computer. 

On my 2014-2015 Chromebox - I have 8gb of ram in it and I have a 256gb M.2 on the way for it. Currently it has Ubuntu 20.04. 

And on my 2010 MacBook pro - I was able to get Fedora 33. Still troubleshooting wifi. 

Next up trying to figure out getting an external USB drive to mount in Plex on the chromebox once I get the new SSD. It's an i3 model so it does ok overall even with a dated chip. 

I really like Chrome OS - but my chromebox which was strictly an extra machine / video caller machine - has been no longer supported since 2019. So I definitely needed to do something to start using it again. 

I have a web background and am very familiar with various CMS systems and for work I work in Customer Success Management - so I am very used to CRM software. Like 4 of each, so it's fun to check out all of the Distros. 

Thank you for replying - I had no idea if anyone would - I really appreciate it. I will post after I upgrade the ssd and get that going. 

Any other folks using Plex with LInux? 

Kevin