The photo of Shousuke and Ai is adorable.
I think the quote is "Tadano sis OP plz nerf". She'd be hell to have decide you need her help, but damn if she isn't fun to watch at work.
I do think Shousuke is enjoying himself, in a kind of annoyed way. The chapters featuring him without Hitomi — particularly 173, where Rei was following him around — have given me the impression that he's the sort to whom everything comes very easily, so nothing is actually interesting. He really does need something to make life difficult.