You can get two weapon fighting from ranger level two, so I'd stick with either fighter or ranger. If you're set on mixing these classes though, I'd go 2 Rogue / 5 Gloom / 5 fighter of choice; that way you still get the extra attacks from the warrior ethos, and sacrifice very little from one thief level.
To be fair, my first char will be a Gloom 5 / Rogue 7 so I'll not go the same route with Astarion.
But. Next on my list is Shadowheart and I want to play Shadowheart as a rogue multi, too - goes great with her Cleric subclass and her secret Sharran operative character. So now I have two roguey playthroughs in a row and will probably postpone Astarion for a bit. But, If I wasn't doing my own version of this, I'd say:
Assassin 7, Gloom 5.
+ Invisible in the dark to all who rely on darkvision [pretty much everything except humans or casters with True Sight] - This means you don't have to spend a bonus action to hide. Helps more for archery, but you can escape into the shadows without having to hide.
+ 3D6 Sneak Attack
+ Two attacks per round [only one sneak attack per round] + Offhand; so even if you miss once, you're going to hit once per round and get your Sneak off.
+ Assassin Crit Guarantee
+ Ranger Casting; Hunter's Mark, Jump, Speak with animals - all good stuffs.
+ All the best stuff from both classes
Edit: And, as Astarion, you can speak with animals, then eat them.
Last edited by rodeolifant; 11/07/23 09:45 AM.
