Who would have to bail the other out of jail?
Honestly, I think Kakashi would be the one to bail Iruka out of jail XD
Iruka would be invited out with his friends for a drink or two, which always ends up being one too many, despite his insistence on only having a couple; and when he’s too drunk to be sensible, his prankster nature really kicks in and he’s suddenly full of great ideas…
Too bad they’re all illegal (harmless, but still illegal); and he & his friends are too drunk to notice that they’re about to get caught, or that the bucket of paint they’ve run off with has a hole in the bottom and is painting a trail right to them XD
Kakashi never expects Iruka home on the nights he goes out (though it would be nice), as sometimes it’s easier for him to just crash at a friend’s place; but if he hasn’t heard from him by lunch, he knows Iruka’s in trouble and he has to go collect him at T&I.
When Kakashi can, he’ll join Iruka on the nights out, to make sure he doesn’t get into any mischief, but sometimes, Iruka can persuade him to join in on the fun, too, and they both need someone to bail them out (and Kakashi will just get Tenzou to do it) XD
I think there would be times when Kakashi gets arrested on his own, as well; but I think it would be for more serious reasons, like an enemy framing him for a murder, painting him as a Leaf traitor, etc. rather than smaller crimes around the village…
Except for when he wants to know something and breaks into restricted areas to get information, and is so engrossed in what he’s found that he forgets where he is; and when he’s done and finally ready to leave, he turns and finds Tsunade or a pair of ANBU waiting at the door for him XD Even better; it’s Ibiki, leaning against the doorway; and when Kakashi makes eye contact with him, Ibiki just sighs and holds up a pair of handcuffs, clearly done with his shenanigans 
What do you think?
I would love a link to it if you don’t mind!