I will have to look in the RR commands and such. I may be able to do some sort of If/then/else statement to fire ONSKINSTART. If nothing else, I could probably create a VBscript/AutoIt Script to handle it.
This way, when RR returns from hibernate/ is bootoed up, it would look at the time in the rr.ini and compare it to the current time when the skin starts, and force the switch, IF it is set to auto switch in the rr.ini as well.
If RR was running at the time that is set in the rr.ini, it would handle the switch at the time you have set in there on its own.