It sounds a little like tying a red hanky to your cock and dancing in front of a bull. Sure, it could be really exciting, and it might be a daring choice, but it's tempting fate and could get really ugly (medically speaking) really quick.
I think this time taking the health risk will work out ... I mean we couldn't possibly be that unlucky, right? ...
He will be fine. Fire the training staff and hire a cleric. Plenty of stamina and healing potions to boot! Sorry I have been playing too much Skyrim.
"A healing spell! Are you a priest?" Hey Lydia, carry DeJuan for me. "I'm sworn to carry your burdens..." My wife is out of town this weekend... time to double down on Skyrim.
It's too bad they'll never fix the bug that'll open up her romance path. I want my Redguard archer/rogue to marry her.