The newspaper photo of Midge's dress being blown upwards does not match the image in episode one. In the photo the soldier on the left and the one lying on the ground are looking at Midge, but in episode one they were looking at the camera when the photo was taken.
Moishe Maisel tells Joel that he met some Canadians in the Army, and that among their peculiarities, "they put cheese curds on their french fries".
The now-signature Canadian dish poutine, comprising french fries topped with fresh cheese curds and gravy, was invented in the 1950s, long after Moishe Maisel would have finished his army service.
Reggie calls Shy's press conference a "presser." Reggie also tells Susie that knowing the details about hotel rooms on the tour is "below his pay grade." Both of these expressions weren't said in 1960.