I haven't tried this yet but I would like to do something similar to the PsuedoTV plugin from XBMC and basically what you have described but randomly instead.
I would like have JRiver create a random playlist of Comedy shows that I could start playing, walk away, and have it still playing hours later.
I would to use the % to have it seed the playlist with certain percentages of designated series with no series playing 2x in a row.
My serie's episodes are all in either the mp4/mkv/avi format.
[EDIT]
Well, I tried doing this and I don't believe Play All is an option for video as it is for audio?!
@icehouse10
I created a Smart playlist of Comedy Episodes and that works fine in building the playlist, BUT, as you said, it will not automatically advance and play next episode. I think I have been down this road before and never had closure....
I believe it all boils down to not having the Play All available for video.