Hriston
Dungeon Master of Middle-earth (He/him)
Then you have to take into account other factors. With non-identical creatures, are they all visible? Are some scouting? Are some built for initiative themselves? Does assassination feel satisfying if used on a weak minion? Non-identical creatures often mean enemy parties or an enemy party and a leader. That leads to a lot of variation in location. It's not as simple as the percentages you outline, at least not in my experience.
Sure, I was just trying to see if my math was close to correct for establishing a base chance, so I was purposely excluding details. I think it really depends on what the assassin rolls.
For example, last week I ran an encounter with a group of orcs, their orc chieftain, and a ranger.
Orcs might have lost initiative. Who cares? You don't even need a crit to kill an orc. Orc chieftain was hidden in cover. The ranger had pass without trace up and a high enough Stealth score the party couldn't see her. So even if you win initiative, if you don't see the target you can't hit the target. That's another strange effect from this ruling. The assassin could win initiative and still not be able to target someone that can't see him same as the target of his attack doesn't get to attack him until he sees him.
It sounds like the assassin doesn't know anyone is there except the orcs, so I'm not sure how the ruling effects that. If he decides to attack, it only makes sense for him to target the orcs. You seem to be saying this is a change, but from what?
What would you do if the Assassin won the Stealth roll, was prepared to attack, lost initiative negating his ability to crit on surprise, then decide to not attack because he didn't win initiative? The target doesn't see him because he is hidden. So can he reset and roll initiative again since the target can't attack him because the target hasn't seen him? How do you work that by RAW? Nothing in the RAW states that the target even if he wins initiative knows the attacker is there until the attacker actually attacks. By RAW he could choose not to attack and stay hidden. Do you just roll initiative again next round or a few rounds later?
Assuming we're only rolling initiative because the assassin has declared his intention to attack, I'd discourage "delaying" for better initiative by using the original initiative order. Another way to look at it is we've gone through steps 1-3 of setting up the encounter, but round one doesn't start until the assassin actually takes his first turn and attacks. The gap in time isn't significant enough to warrant rolling initiative again in my book.