I'm running Plex as a media server here. It works fine, Are you sure that the video format is right for your flip TV box? I have a Telstra TV and a Fetch TV box and some videos will play ok on one box but not the other. I'm still learning the ins and outs of plex so am no guru. Son (who works in the AV industry) tells me that plex may need to be told how to transcode the video for my Fetch box, but I am yet to work out how.
One other point, which may not be relevant, I am running Plex under Linux Mint - I have weaned myself off Winwoes a looong time ago.
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