Responses
I doubt it. He's aware that making a person a shadow changes who they are fundamentally. Like with the healer who died on jeju Island. So, I think he knows she would be a shadow of who she was in real life (no pun intended lol). That's why in the first timeline before he knew he could turn back time if someone he cared deeply for died (ie go gun hee) he didn't turn them then either. The only two humans he made shadows were iron and the brother that was trying to kill them, and he hated those two.
Just a thought, jinwoo is immortal and he is just changing his appearance to look like he ages. I wonder what will happen if Hae-in died of old age? Will he make her one of his shadows?