@hellogoodbye thank you for all that info! These all seem like solid options.

I think I would prefer organization as well. Plex drew me in because of the fancy covers. I am somewhat familiar with Kodi - I had a sweet little firestick set up for a while, but I found the speed almost unbearable.

I am totally open to other solutions. In reality, I could probably just set up some kind of NAS, because most of my viewing will be staying home... At the same time, I do really like the portability of a cloud based solution. Apparently I need to do a lot more reading