My 2nd time around doing these quests and I'm trying to do them without anyone else around. Problem is, this wandering Khajiit mage and mostly everyone else I've stalked never seems to sleep or do anything by themselves? Does waiting break this, since I usually wait outside if it's daylight 'til night and they just wander around outside

If you cant get them to go to sleep (ive killed many a target asleep) then crouch and wait until you are hidden, in this narrow time frame take a shot with your bow or stab with a dagger and get out of there. then come back in a day and all is well, no bounty....unless you brought lydia with you....so many bodies.

The game doesn't penalize you for blatant "LOOK AT ME IMMA KILLIN'" kills, so it's kind of a non-issue.

Eh, I know that much. I kill guards within plain sight of eachother, just wanted them to be asleep before poisoning them.