1) Why not just make use of iCal or set Cron/CronTab? Rather easy, you don't need to worry about Energy Saver. You can run a Bash script to quickly change user/prefs, etc. and Automator allows you to tie all these basic OS functions together if you want. Technically iCal does everything your asking. You might need Automator to tie a few things together depending on how you 'decide' to work. Anything that needs to be done at system level can be handled with Bash.
2) I think you're making this way more complex than necessary. For example, the way iCal works on the system, it can remember a birthday or any other event and act on it. Good so far, right. You can have as many events on a day. In simplest rems, a text file holds the pertinent information. The system Launchd or/and Cron/CronTab handle the scheduling from another text file. You don't have to worry about looping this way. Heck I deploy entire systems and change modules this way daily. Its very efficient. Automator gives you access to all these parts of course, but it may not be the best approach. Your call.
The main thing I'm suggesting: Look at what the system already does and how it does that. Either replicate or use it to your benefit. Do this with all things in life and save yourself headaches. If you really have a function that doesn't exist, then you have value in the app your stitching together.
All the best.
“Pathetic Earthlings. Hurling your bodies out into the void, without the slightest inkling of who or what is out here. If you had known anything about the true nature of the Universe, anything at all, you would have hidden from it in terror.” ~ The Emperor Ming
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