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I had a similar set up for a while. 3 modulators, one of which was connected to a TV-out on a PC. Nowadays, you could use a HDMI-to-composite or VGA scan converter to get your PC's signal downgraded to composite level.
Many media players have a playlist repeat function. Just add all your videos, set it to play full-screen, and set the list to repeat.
Beware though, all that equipment running 24/7 will make your electric bill creep up.
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