I finally got around to setting up a PC to play videos the way I want them played. It was harder than I though it would be at first, but I came up with a simple solution that works for me.
I use VLC player. I had to find a plugin to merge multiple playlists.
I have a playlist with a couple thousand 80s music videos. (Thanks Yotsuya!)
I have another playlist with 30 second MTV bumpers. (Thanks again Yotsuya)
I have a third playlist with 80s commercials.
Finally there is a playlist with PSAs and Schoolhouse Rock.
The Multiple playlist manager takes these lists and merges them into 1 master playlist in the order I choose or I can randomize each of the playlists that make up the master playlist.
Mine is setup to play 3 music videos, then 2 commercials, next 1 PSA or schoolhouse rock segment, an MTV bumper, and then loop back to 3 music videos. etc...
I can save that playlist and run it as is or I can edit it. Every time I run the manager it creates a new randomized playlist.