Perhaps Astarion looks like Cazador's friend
I have seen a lot of people headcanon Astarion looks like Cazador's former master Vellioth, which does make a lot of sense. However, I've always had another headcanon:
Perhaps Astarion looks like that friend of Cazador who was drained and killed by Vellioth.
In the 5e DnD Monster Manual, vampires have the nature of Dark Desire, and it says "Whether or not a vampire retains any memories from its former life, its emotional attachments wither as once-pure feelings become twisted by undeath. Love turns into hungry obsession, while friendship becomes bitter jealousy. In place of emotion, vampires pursue physical symbols of what they crave, so that a vampire seeking love might fixate on a young beauty. A child might become an object of fascination for a vampire obsessed with youth and potential. Others surround themselves with art, books, or sinister items such as torture devices or trophies from creatures they have killed."
And it seems evil aligned creatures in lore always see friendship as vulnerability and weakness. Vellioth punished Cazador for his connection to his friend by draining this friend to death, and taught Cazador to never let anyone be his equal. This friend must be really special to Cazador to lead to Vellioth doing this.
We know that Cazador is a pretty good student for Vellioth's lessons. He learned the lesson and killed Vellioth. And he's begun to see the friendship he once possessed as his vulnerability and weakness. He probably hated being punished by Vellioth for his vulnerability and he wanted to vanquish his weakness by torturing someone who could serve as a symbol of his vulnerability, someone who looks like his friend.
He might still have some special emotion, even some kind of love, towards his dead friend but his dark desire has turned his emotion into hungry obsession. So, when he saw Astarion, who looked a lot like his friend, Cazador couldn't help being attracted to Astarion but also he wanted just to possess him, belittle him, and torture him.
That explains why Cazador has this special favoritism towards Astarion in terms of torture and punishment. In fact, I somehow believe that Cazador chose all his spawns because he had some affection towards them all. But his feelings are totally twisted so that he would torture them and use them, while insisting they are a family.
I don't know whether it's true that Cazador sent the Gur to attack Astarion, but I think he did savor the moment when he turned Astarion because he now had the power to "save" him from death, and to turn him into his own possession.
His torture is not merely some sadistic hobby but quite calculated and cold according to his journal. It's only when Astarion got away that he showed emotion. It seems like he was subconsciously training Astarion as a potential successor, just like Vellioth taught him and trained him to be the vampire master of the Szarr family.
This reminds me of the 5e DND module "Curse of Strahd". In "Curse of Strahd" if you role play as Strahd, he has an objective to find a successor, because he thinks if he can find a successor to replace him then he can get rid of the eternal curse and get his freedom.
After you defeat Cazador without Astarion you can detect his thoughts, and you will find that he also thinks he is forever trapped in this immortal curse. He cannot rest and he's in grief. He wants to break the curse, and that's why he sought the profane ritual so that he could gain the ability to finally "live" like a mortal.
But apart from becoming the vampire ascendant, there's another way of terminating his grief to finally put him to rest, that is, to be destroyed and replaced by a successor.
In some way, he was subconsciously expecting Astarion to succeed him and replace him. I think his former master, Vellioth, knew it even more clearly that he would be replaced by Cazador somehow, and Vellioth was training him to do that by intention. Cazador was doing this similarly but more unconsciously. In his subconsciousness, either he would consume Astarion at last, or Astarion would end him and replace him.
Finally, and this is purely headcanon: according to Astarion's age, he was probably born after Cazador's friend was killed. If this friend was also an elf, then when Cazador saw Astarion, for a moment he might think Astarion could be his friend's reincarnation.
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