A total of 5 shots are fired from the sawed off shotgun that holds 2 rounds. Two were while Tom was fighting with the gun thug, then a third by the gun thug after Tom began to dig his own grave, and then Tom fired two more to gank the gun thug.
Reddington and Kaplan are side-impacted by the gun thug's car. The windshield of Reddingtion's car is cracked as if his head had hit it. On a side impact, the occupants are thrown to the side, not forward. As such, his head injury could not have happened.
When tom is in the trunk of the car it passes a truck and when they show the car passing the camera and crew are reflected in the windows.
Tom tells Aram to track the car radio of the "50's Dodge sedan" which was actually a 1967 Dodge convertible. The technique Aram used to track the Dodge fails on account of three things- first, by the late 60's, American cars no loner used tube radios, second, even f it were a tube radio, Tom would need to have access to the inside of the radio, requiring it to be removed from the dash. All Tom did was pull a speaker wire in the trunk loose. Finally, such a signal would be too weak unless there was a receiving antenna within a few miles. Cuba has no such infrastructure.
Tom, a skilled operative, does not realize the sawed off shotgun was fired twice while he was fighting with the gun thug that was to kill him. As such, it was empty and no threat, yet Tom did not try to take down the gun thug until he began digging his own grave. He could have ganked the gun thug and then jacked the pickup and pursued his daughter.
It makes no sense for the Cubans to release the prisoners from the torture prison they don't want anybody to know about. The prisoners are all witnesses and their release ensures knowledge of the facility must become public. The logical thing for these henchmen of an autocratic, unjust and inhumane regime would have been to kill all prisoners instantly.
Tom calls the car a 50's model blue dodge sedan. In fact it was a 1967 Dodge convertible.