Astarion fits well as a Gloomstalker.
Build 1: (Assassin Gloom)
3 Rouge (Assassin) > 8 Ranger (Gloomstalker) > 1 Rouge (Assassin). You get 3 ASI this way. Plus he can use his sneak attack twice (Once via bow, and then close the distance with the sneak attack crit).
(1 Extra attack due Ranger comes online at level 8)
or
Build 2: (Rouge Fighter)
Rouge > Fighter 11 (Battleamster) (You get 3 attacks as standard at level 12 without haste or action surge). Yea you miss out on the ability improvement, but you are a battle master 9 attacks when you are using action surge + haste cast on you. Fighter also gives you an ability improvement anyway to make up for it.
(2 Extra Attacks due to Fighter. Build Comes Online at Level 6 with 1 Extra attack + another at level 12)
Build 3: (Raging Rouge)
(2 Extra attacks due to Beserker Barbarian comes online at Level 8)
Rouge 3 (Thief) + Barbarian 8 (Beserker) > Rouge 1 (Thief). You can make use of the Bonus action as Beserker Barbarian to Extra attack or Throw something nasty knock people prone.
(2 Extra Attacks due to Beserker Barbarian + Theif combo. Build Comes Online at Level 8 with 1 Extra attack, and you get to use the two Bonus actions for extra attacks.
Note: you can make Astarion into an Arcane trickister but that class only really comes online at level 9 when enemies have disadvantage against your spells.
Last edited by kingsims; 14/07/23 09:39 AM.