Add: On the 29th. Before he went to the pharmacy,he called for a cab to come to a location ????away from his house. Said he wanted to go to Philly.
Something happened between that phone call and the time he went to the pharmacy to make him change his mind about taking a cab to Philly into going to Wil to pick up his car. (driveit to Philly)
It takes about 15 minutes for a man of Jack's stature to walk a mile. It is about 8 miles from the Pharmacy to Wilmington so it would have taken Jack 2 hours to walk it.
It also means he was robbed damn close to where we see him in the garage in Wilmington (2 miles at the very most). Of course that leaves no time for Jack to recover from being "robbed"....so he was more likely within one mile of the garage.
I think the change of mind to just get to Wilmington is because there are hotels and cabs all over the place. It simply increases his options. He's only an hour behind schedule when he leaves the Pharmacy.
I'd check all the cameras withing a mile of the Pharmacy....all along Rte 9 to Wilmington and concentrate on the last mile before the garage.