I loved that you tagged the gif set of Oliver saying he's the weapon as mediocre mentor because when he started trading Roy is complain at the tv "you don't tell a student to do something without telling them why they need to do that". It's one of the 1st things you learn as a teacher.
(I hope you don’t mind me publishing this. It got kind of long and rambling.)
Oliver tries, he really does, and he’s slowly getting better, but he’s just not a good instructor in the vigilante arts yet. :)
I tend to use the “mediocre mentor” tag for scenes when he employs the techniques that his teachers on the island – Yao Fei, Shado, Slade – used on him with his own students. But Helena and Roy and Barry (and, arguably, now Ray) don’t need the same kind of harsh kill-or-be-killed training, and it’s not actually helpful for the situations they’re in now.
I think that’s a part of why he keeps refusing to train Laurel. He doesn’t want to use those methods with her because he still wants to see her as the girl he left, the girl he pinned his will to survive on for so long. If he helps make her like himself, then everything he’s done to push her away from his own slow self-destruction – all the way back to his repeated cheating on her in college – will have been for nothing. He won’t have protected her from anything. He keeps forgetting that she is capable of protecting herself.