I agree with theschnauzers, it's just a super leg, so don't overthink it...
And yes, if you arrive at the pit-stop without something you need to pick up (items), Phil will send you back to retrieve it. Not with paper clues though, if you lose the paper, you need to have the kindness of other racer to tell you where to go... and if none of them wants to help... good luck.
On Leg 10 of TAR 10 in Morocco, Tyler and James were running to the pit-stop and forgot their lucky pendant... before Phil had to ask them to go back and retrieve it, they realized their mistake and went back.
