I don't feel badly towards Haesoo about it but you're spot on about his tendencies and him being essentially stuck in place. I think even he is frustrated with himself. He realizes it with his dissatisfaction with his writing and career plus all the angst with Joowon. The question is where to go from here, stuck in the same old dynamic. Being someone new, Taku clearly offers an out. But is that really what he needs? Rather than whatever pairing is endgame (if there even is an endgame ship like that) a fundamental aspect of the story here is Haesoo's development (or regression) as a character. The relationships he gets into are just one aspect of that.

... The more I dislike Haesoo's behavior. Or well, not per se. But I still want to slap him really hard in the face to wake him up. He's just walking in a terrible place of his own making. I'm not saying Jowoon didn't contribute to it, but I see waaay too many people putting it all on him to my liking, as if Haesoo's only wrong had been to stick around. I'd probably feel the same about the other characters were the focus on their thoughts, but it's not half as much.
In the end I don't see this story as a shipping thing, especially since I don't feel there's much suspense regarding that (alone or with Taekyung I think); but rather as a story about Haesoo's cynical, undecisive, brooding and bitter mind. Will he get better, that's the question I'm the most curious about.