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As soon as he gets a little nibbly, I get a little stabby.
End of use for Astarion for me XD.
Regardless of my… vocal opinions regarding the character (I really don’t like him, no matter how good he has been voiced, and he has been), Astarion can hide and inflict massive damage before and during a fight, multiplying his damage and utility, to the point it is possible to make him a murder machine. He cloaks, he stabs, proccing a one crit hit KO, while remaining “invisible”. Rinse and repeat.
If you press shift you can see the "line of sight" of enemy units, aka the red area. Wherever the red area is, you cannot use hide.
Rule of thumb: you can only use hide when the enemy is not seeing you.
In combat you position Astarion therefore at the flank and make him attack with advantage from the side or behind the enemy.
You can not always use hide, as some battle areas are unsuited for it.
Like, having enemy rangers on the other hand who make it impossible for Astarion to hide as long as they overview the field.
But in close quarter it is all about "fighter engages enemy , Astarion goes behind enemy, hide and attack"
While the advantage attack is strong, it is not the only way to play thief/rogue - the thief is strong because of the extra bonus action, so it normally looks like: one bonus action to apply poison on the dagger, stab with normal attack, stab with the extra. And the turn after, stab, stab, stab.
Does not always have to be an advantage attack with hide for that to be strong.
Also, you don't need to hide to use Sneak Attack, the bonus also applies if one of your allies is in melee with the target.
It's Astarion!
As for how how use him, just use Sneak Attack every turn.
You can hide but you don't have to, just employ the other method that allows Sneak Attack to be used.
Just move another character close enough to the enemy.
But I finally decided to try something entirely new for him - as a mind weaver void reaver, he now uses a variety of cripping psionic attacks that combine dual wielding psi-blades with his eager embrace of illithid powers. I still made sure he kept skill proficiency in sleight of hand, and such things.
I also have Lae'Zel as a forceblade mind weaver, which makes her the psi warrior I think she should be. She won't use illithid powers unlike Astarion, but she has her own ways of psionically defeating the ghaik.
Oh damn, it's Mander! Hi Mander!
But in general, you get bonuses to hide from any gear and avoid disadvantages from armor etc, and then its a matter of getting out of line of sight, burning an action (cunning or no) to hide, then rushing in to stab, repeat each round.
-> you can backstab without hiding by having some other character in combat with the target. This other character can be a pet like shovel.
-> later in the game there is a ring that grants advantage on all attacks!
-> there are a number of items that grant invisibility and a lot of the shar junk adds a lot of power if you are obscured (start finding it in bulk in act 2)
The sneak and stab idea works but it costs an action that should have been an attack. Its not a great way to play because of this. You really want to figure out how to do sneak attacks without having to hide to get the most out of a rogue, and even with that, a 4th attack as a warrior / rogue split usually ends up superior to an all rogue build -- the sneak attack damage does not keep pace with another attack after the early game.
Stealth is optional. I barely touched it in my last playthrough despite having both Astarion and my Tav putting in a few levels of Rogue.
Have one of your melee characters(Or a Familiar like Shovel) get into melee range with an enemy so they are threatened, and have Astarion attack them with a bow/dual hand crossbows. As long as the enemy is threatened, or Astarion is hidden, he will get sneak attack and deal MASSIVE damage to enemies.
Also, his story is quite good. Yes, he can be insufferable, but for me that means the voice actor for him is great as his job(He's supposed to be insufferable.)
I use Astarion like this.
1) He stays in camp all of Act 1.
2) I bring him to Moonrise Towers so he can bite the blood lady and I can get a +2 strength potion.
3) He stays in camp the rest of the game.
I did take him to fight Cazador once, just so I could see what that was like.
As I also do. For the plants close to where you first meet him on the beach.
Astarion is with me the entire game because the damage he can put out at range and up close when other members are flanked is *chef's kiss* And lock picking is his schtick. He gets all my sleight of hand gear and dex stuff.