Thanks for the ping, Albion!
I see Jack’s behavior as a man trying to escape.
For example, when he asks the pharmacist for a ride, he leaves when the pharmacist offers to make a call.
Could this mean Jack thought the pharmacist would turn him over to authorities that were after him?
The same at every stop.
He was looking for his attorney....why...did he want to give some information that could be revealed in the event of his death?
The trip to Madrid could be Jack himself, trying to setup a diversion so they would look for him at the airport.
All these things make sense if someone powerful is after you.
I agree; he appeared to be trying to elude pursuers in the tape. As for the Madrid angle, that would depend on the date of the purchases.