Playlists do not show what the last watched item was and will not continue playing from the next episode/movie.
My wife and I experience this on the PC, PS4 and Xbox, so it is not exclusive to just one player. As you can see in the screenshot, there is no way of knowing what has been played and what has not. The last watched in this example it S3 E11 but when you have a large playlist like this one to go through all the shows and episodes to find where you left off so you can continue is frustrating.
Playlists have never done that. There is a feature request that you might want to vote for.
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