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Honestly, I want the assassin's auto-crit changed to "on any target that the assassin has the Hidden condition against." Then ducking in and out of hiding for lethal sneak attack crits would have a pure assassin rogue's damage output keep at least close to other martials, and with the right items, buffs, or multi-class combinations make it the single best option for... the thing it's built to do: Kill singular targets from stealth.
Since attacking removes stealth, that guarantees you're not mixing the auto-crit with multi-attack and action surge and such too, so it would encourage using it with high damage single target abilities... like sneak attack, smites for oath-breaker multiclasses, and high damage spells that make attack rolls. It wouldn't even be any more broken than the existing auto-crit mind-flayer ability. Just an option to get a similar capability without the tadpoles for someone building their class to it instead.
The main thing to note is that Rogues have the BEST Criticals. Because when it comes to critical hits, all the DAMAGE DICE are doubled. And a level 11-12 rogue is getting an extra 6d6 damage from sneak attack, so that's 12d6 extra damage on a critical hit. And they can do it every turn, all day, every day.
But how do you get those crits? Easy... Poison. Drow poison specifically. Carrion crawler poison later on. Hold person, that one murder ring, a particular Illithid power... it's not that hard to guarantee a crit.
You need to toggle "Sneak attack" to (ASK) instead of automatic, that way, you can make an offhand attack with a drow poisoned dagger and DENY the sneak attack. And when the enemy gets poisoned and falls asleep, you can make your main hand attack and accept the sneak attack.
There's a neat bug, that if you make the game ASK you if you want to sneak attack someone, it counts as a second, completely separate instance of damage! Why is this important? Because of a magical shortsword that does +10 necrotic damage on crits. If you make the game ASK you if you want to use sneak attack or not, instead of using the "Sneak attack (Melee)" Button, that particular shortsword will give you a SECOND +10 necrotic damage.
Okay, you can't get crits all the time, and you can't get surprise all the time.
It's not the best.
But the class works and it's fun! I solo fights for ♥♥♥♥♥ and giggles by disappearing in the shadows and making enemies completely lose me, only to jump back in and stab away
It's rouge not rogue
On if he is carrying a baton as a weapon.