This is a great solution. I'd have to add that Plex supports sync into whatever cloud system you have as well. You select which content you want duplicated and it takes care of the rest.
I did the same as the original poster, converting lots of VHS and other dead media as best I could. Installing Sickbeard, NZBGet, Couch Potato, Headphones and a torrent server it's become quite a thing to behold. Using Plex with a couple of Chromecasts around the house really makes things easy. Chromecast and Plex get along with each other in a brilliant way. Best $35 ever spent. Even with the Netflix, HBO Go, iPlayer and a ton of other apps that just work.