Depends on how Dru wants to play it. I feel like there shouldn't need to be a check to determine whether someone has a scratch or has a deep, bleeding wound. I see HPs as just a numerical representation of the PCs condition. I'm content to know if someone is unhurt, scratched, wounded, badly wounded, or dying. If he sees a crossbolt sticking out of one of his companions, he'll probably try to heal them.
That said, if Dru wants Heal checks before folks tell me their HP, I'm happy to make them.