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it possible that a team left for the next leg before the last team checked in on the previous leg?

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Could be possible. May have happened in the past. It depends on the hours of operation, flight schedules et al in the set-up for the next leg of the Race.

Production would have to know some cutoff time where they would have to cycle through an extra 24 hours at that pit stop before continuing. That is why they build extended pit stops into the Race. If a non-extended pit stop has to be extended 24 hours then the next projected extended pit stop will be reduced to the standard issue 12 hour pit stop. The Race then goes back on track quickly for the production plane tickets, film permits, hired local task safety/adventure companies, extra local zone camera crews etc down the rest of the race course.

But, like I said, it could be possible that lead teams depart before the last team checks in and is eliminated IF Phil can get on that plane with the lead teams or IF an "hours of operation" or "ride a bus for 20 hours" will hold up the teams enough that Phil can leap frog them in country and get to the next mat ahead of them.

He usually does stand-ups at the detour and roadblock points etc but sometimes they are filmed after the last team arrives like in Sicily in TAR9 with the statue roadblock. There was no time to do the stand-up before the first team would be arriving so that stand-up, according to an interview with Phil, was filmed late at night after the fact.

Worst case I imagine he could add a voice over to a detour option showing hands with clue, close-up of items to be used etc in the post-production and most people wouldn't notice the difference.

The only place he has to absolutely get to ahead of the first team is the mat. That was why in TAR1 he did not greet the Racers except to eliminate the last team. Production was worried they couldn't pull it off getting him to the mat always ahead of the lead team. But they somehow did so starting with TAR2 onward he greets everyone though sometimes with only a minute or so to spare.