Backup Strategy and MS Scheduler

So I’m trying to get more regular backups going. I’ve searched through some of the older threads and I’ve got a few questions.

  1. Synctoy vs rsync (maybe something like deltacopy). pretty much a pure windows environment with multiple machines needing to be backed up. Any advantage using one over the other? For now I plan to just use an external usb hard drive for backing up to but maybe someday I’ll setup freenas or something then that built in rsync server would come in handy. Is one faster than the other?

  2. MS Scheduler. Backing up 24/7 machines regularly should be pretty easy to schedule. But what about my wife’s machine which is only turned on when she uses it? Here is the scenario. I want to automatically backup her files once a month. But I don’t know when the machine will be on. I’d like to say run synctoy or rsync on the first of every month BUT if that event is missed (say the PC is never turned on that day) then I want it to fire off the backup the next time it is booted. Does MS Scheduler let you do something like that or is there an alternative?

I guess I can just write something really quick but was just wondering if the solution was already out there.