I've been lucky. Came across 4 canteens, extra food, a Winchester with 45 rounds and still have a clip or two for that crappy Makarov I've been carrying around since before the start of the no weapons when spawning thing.
Schumacher will have very good pace, but I imagine he will get caught in an incident (may or may not be his fault) that puts him at the back or completely out of the race.
I don't think it was exactly realistic to hold off Maldonado for another lap and a half. Hamilton's tyres were shot and only getting worse, so it was only a matter of time before it would've happened. That said, Maldonado was a bit foolish to think he was getting through there.
IMO the worst is when you gather plenty of supplies (I usually get 3-4 full canteens and a lot of food) and set out to finally gather some good weapons and military goods, just to be lit up by some camper and have to start all over again.