(Should probably say while I’m thinking about it, my Kaito does tend to be more aware of his loneliness. Not normally, but the reason I do have a lot of random interactions at other people’s houses take place after heists is because that’s when he feels it most. Again, since my Kaito is more independent as the manga would indicate, and doesn’t have anything like a post-heist chat with Jii, he tends to go home himself, and after a heist full of people to come back to an empty home (with any targets always being failures), it does get to him. So, that’s why he’ll almost always be after a heist in popping up in people’s windows. Or, if he were more bold, through the front door. :V 

(And aside from those, normal days would have him coming home after walking with Aoko or such, it’s more doing it in the dead of night after he’s been against everybody when it’s not the same level he can deal with. So yeah, if he’s not visiting, he might stay out a bit or at least on the roof or such. Not as bad in the open as it is surrounded by walls, though the ‘Kid cave’ isn’t so bad.))