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Plex is so awesome, I can't properly describe it. I've subscribed to the PlexPass simply to show my appreciation to the developers. For me, it's Plex + a Roku 3 though.

Does it work with subtitles?

Yes, but it takes a while to get set up right. I think this will make it work:

https://forums.plex.tv/index.php/topic/90563-roku-not-playin...

It does have the option to hard encode subtitles when it is converting media and there is subtitle options available but I have never used either of those features.

What are you doing with Plex + Chromecast that expands the capabilities of a Chromecast?

I can stream my library of videos (no Netflix etc. here in Switzerland) from any of my devices to my Chromecast.