One other small advantage Cloud has - he grew up with only his mother watching over him. He probably learned very early on that there were certain times when things got much stricter for no readily discernible reason, and learned those times were when he really needed to be either on his best behaviour, or at his most elusive, or, for preference, both. So in other words, he learned about these things young, and as he grew up and found out the reasons, he was able to take better action to deal with the consequences.
It figures he'd be the type who'd notice the signs and symptoms, and also take note of preferences in remedies. I like how he's just very quietly going the extra few steps (nothing massively out of the way, just the little things which count) to make her day as comfortable as possible.
About the only nit I'd pick at this point is that Cosmo Canyon is on the far side of a completely different continent to Edge, and thus wouldn't precisely be the ideal destination for a family outing (the equivalent is a family in Moscow deciding to jaunt over to the Grand Canyon as a day trip). I'll presume the arrangements for cancelling things involved a few calls here and there, such as cancelling a trip on the Shera and maybe letting Nanaki know their rooms at the inn there wouldn't be needed. [NB: I'm a paid-up member of the Overthinkers' Club. Feel free to ignore me on this matter.]