This is fascinating!

I've been struggling with an issue myself where I have a non-24 hour sleeping pattern. Does your system handle changing of timezones gracefully? It's almost like my timezone changes by 1.5-2hrs every day, and sometimes stressful days will completely throw it off.

Figuring out how to stay in sync with a 24-hour world has been a thorn in my side for ages and I think planning like you're doing would help me tremendously. (I actually clicked to read the comments on optiplanner to do something very similar to what you've been doing!)