I actually think it was possible for a solo victory in the Amelia Earhart run. If Scott started in the Cave of Sighs and followed Kristen's path, then he would've only encountered the guard in the Swamp. And while the path was long, most of the room were super easy. Which is why Kristen still made it one room away.
And for the Pirate Captain run, it wouldn't have ended up being one of the best wins on the show and people would probably overlook Jessica and Jarrid's strong performance despite the disappointing outcome if he did get captured in that room.
What if Ron was caught cheating in the moat in the Anne Bonny episode?