I love me some winter camping, and I know many people I'd call experienced who don't know how to do so properly or people who don't mind being covered in dirt, rained on etc just can't endure the cold.
30s and such, you aren't at real risk until you stop moving, if it's raining then you need to know wtf you're doing or it's a safety issue. I am not trying to humble brag but I know what the fuck I'm doing, have the gear etc, if I saw rain coming in that weather, I'd call things off because it's just too easy to fuck up.
Phil... well, we know he's got no skills, no gear, and a massive pussy. This leads me to a theory, maybe he's inflating the costs so he can take a woods selfie and stay in a plush motel while Toren drinks himself warm?
Phil would be at most risk at night, as the body kinda cools as it sleeps and you aren't active. Couple that being soaked in freezing, that's how people go. Aside that we know Phil is a sloth so he wouldn't be strolling around doing antics in the woods, probably posting on FB till his battery dies then gorge on cheese and nap.
If he really does this as he says he would, I really wouldn't rule out some injury.