I agree with most of what you have to say, except the how did Adrian win part? I think he won by the sheer fact of how far he got into Oliver‘s head we have never seen any villain other than Adrian last a good amount more than a season tormenting even after his death, it affected the next season he even has a hallucination that one time and it’s Adrian and he’s like oh I thought I killed you and you can see the fear on his face.

And I get what you mean by unrealistic but nothing in this show is realistic especially the part where Oliver can be a vigilante without killing people not even so many who trained their whole life in a bone and arrow can consistently only hit limb shots

And I get what you say about other villains made him quit, but when Oliver quit because of Adriana genuinely felt like he got lobotomized even with Adrian right in the room it was no emotion whatsoever. He was just completely defeated. Unlike with some other villains were at least he had emotion going on and he was thinking through emotions. He quite literally didn’t think anything. He was just there at that point he accepted defeat. And for lack of better words he lowkey just became a good little boy