I'm A Banana
Potassium-Rich
I agree with you conceptualization, but not your approach, as it can lead to being able to get of 3 attacks before the target has a chance to act. I rather prefer, in those cases, just to set the initiative of the ambusher to go first, and roll from there. This is just an automatic win of the ability check, and, since you as the DM have determined there's no uncertainty in who goes first, is still within the spirit of the rules.
However, as I've come to this conclusion while running a game, I haven't made any changes in my current game and still roll initiative and try to muddle through the weird corner cases as best as I can.
That sounds like a fair approach to me, too. I personally don't have a major problem with the character possibly getting off a reaction attack + a round of attacks if they spend the time and effort and risk of (1) separating from their party, (2) succeeding on a Stealth check, and (3) being comfortable with waiting until the trigger activates, to have the chance of (4) rolling higher on initiative. It's kind of a lot of hoops to jump through, and a lot of risk, so I'm OK with a pretty big potential payoff there.
ad_hoc said:Sorry, I'm not following.
I'm treating "Surprised" is a technical term in 5e when it comes to the Alert feat. "Surprised" means you can't take an action on your first turn. If you're immune to surprise, it doesn't mean you notice or are aware of things you otherwise wouldn't notice or be aware of, it just means that you can take an action on your first turn. (It also means assassins get their benefit against you). With the "readied action" model of an ambush, this still gives the ambusher some benefit for successfully going through all that preparation (the readied-action attack), and still gives the Alert character a benefit for that feat (they don't miss their first turn in combat, and if the ambusher is an assassin, their feature gets negated).