What you describe is almost NOT automation. Anything that requires that much attention and supervision, might as well go ahead and be live.
You must be a little older than me. I worked for a station that had an automated FM, reel-to-reel tapes, the cart carousels, the whole bit. Whenever it was programmed correctly, it would usually run well with a minimum of checking up on it. Only problem was that it just SOUNDED automated. It was the early '90s, and this setup was straight out of the '70s. Good thing that it (usually) required minimum supervision because we were running the AM live at the same time that we were responsible for whatever was going on over the FM station. (I could usually just look through the window to see if the reels were rolling, or the cart carousels rotating, or whatever.) The system NEEDED updating, but that would not happen until right after I left that station. Because of the reel-to-reel tapes, we had little real control over whatever song happened to be playing over the air at any given moment. There must have been enough variety on the tapes, because I never heard any concerns about rotation, or certain songs coming up too much, or anything like that. The Christmas music on the FM was probably better overall than what we played on the AM, but it was just your typical Christmas music, only it was on those reel-to-reel tapes.