This is a strange one and I was able to solve it so I am putting this out there in case someone else runs into the same issue.
I downloaded a video that was in MKV format. I have two Plex user icons. One (the Master) is for me and requires a password to enter. It is for my use so other household members do not get into it and mess with the settings. The other user icon shares selected libraries with the master. Using Tivo I was able to play the MKV file on the Master Icon, but not on the subordinate icon. It showed up in the subordinate icon, but it simply would not play. After a brief period I would get the time out error message. The odd thing is that the video would play in either icon on my Samsung Tab2, Tivo seemed to be the problem. I used a piece of software called the Total Movie Converter that I acquired some time ago to convert the MKV video into the AVI format. Now the video plays fine on Tivo in both icons. In addition, the AVI format takes up about half the Gigs that the MKV does. So problem solved.
