When Jack pulls up next to the bus stop Kate gets up and walks over to the car without her backpack. In the shot of Kate getting into the car, her backpack is no longer on the bench, but is magically in her hands even though she never went back to the bench to grab it.
Jack states that he got tickets for Bruce Springsteen "This Saturday" which would have been Jan 31, 1998 (the Superbowl was played on Jan 25 1998). Bruce Springsteen did indeed play in Pittsburgh in 1998, but it was Monday March 2.
Jack dies on Super Bowl Sunday (which takes place in February) in Pittsburgh, PA. The family holds an outdoor, graveside service at the cemetery, where there are leaves on the trees and bird songs can be heard. In February, there would be bare trees and no songbirds in Pittsburgh. Later, the family visits "Jack's Tree," and snow can again be seen on the ground.
When buying a new car from the dealership, the scene takes place in the what appears to either be the very late 80's/very early 90's yet in the background a brand new Tesla and other cars from the 2000s can be seen.
The Bruce Springsteen tickets that Rebecca looks at are for January 31 1998 at Benedum Center, Pittsburgh, PA. However, Bruce Springsteen was playing the Count Basie Theatre, Red Bank, NJ on that night.