How would you adjudicate an attack on a sleeping target? What skill checks would it take for an assassin to sneak up on a sleeping victim and strike?
Step 1: Does the sneaking party need to make a Stealth check? If so, is it opposed by the would-be victim's Perception? And if so, what penalties does the victim suffer for being asleep (or what bonuses does the assassin enjoy for the same reason)?
Or would the difficulty of the Stealth check be based on the terrain instead (like a creaky wooden floor would be harder to sneak on than a concrete floor)? Failure indicates the sleeping party gets to make a Perception check? Or maybe automatically wakes up?
Step 2: So, our assassin has reached his target. Do we roll for initiative—Cool for the assassin versus Vigilance for the sleeping victim? Do we upgrade or downgrade—or give boosts or setbacks—to either side due to the victim being asleep? Or does the assassin just get a free strike, as if the victim were staggered?
Step 3: Let's assume our would-be victim detects the assassin just in the nick of time. Can the victim perform any actions, or does the grogginess of having just woken up warrant the staggered status effect? Or maybe the disoriented effect?
Final question: How, if at all, would any of the above change if the sneaking character were trying to steal something off the sleeping character instead of kill him?