Sanji would go all out in cooking the most nutritious and delicious meals for Usopp to help him recover. He might also be a bit overprotective, not allowing anyone to disturb Usopp while he's eating. Chopper would be in full - on doctor mode. He'd be constantly checking Usopp's vital signs, giving him medicine, and trying to figure out the cause of the sickness. Robin would be quietly researching any possible cures or causes, using her knowledge of history and ancient texts.
Most of the time, it doesn't. However, certain specific settings or applications could potentially send a notification when you exit someone's private story, but that's not the norm.