Factual error: A "wonky" whistle doesn't sound like a slide whistle, it should sound like a weakened version of the correct whistle mixed with the hissing sound of steam. A "wonky" whistle would also leak steam constantly instead of being blown like a normal whistle.
Continuity mistake: When Thomas goes back to Maithwaite, Flynn's railway wheels are not touching the rails, but his tires are.
Continuity mistake: After Thomas stops near the bridge, he does not have a Wonky Whistle.
Answer: Butch the breakdown truck must have pulled Gordon's tender all the way up the rails so the breakdown train can reach it and also Butch helped to get Gordon close to the winch.