Revealing mistake: In a shot of Henry going around a bend in the country, you'll notice that the other side of the coaches is seen painted tan but the other side is painted green and white. This is because of budget limitations.
Continuity mistake: US Only: Henry reverses on to the siding, then he leaves it again. His tender also hits the station building.
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.