That Rockwell painting is obviously pre-D Day. The map on the dad's lap seems to indicate an arrow representing Allied invasion of mainland Italy.
Probably painted in the fall of 1943 is my guess. Still a long way to go before VE Day. Hell, a long way to go before the liberation of Rome.
P.S. My youngest DS is currently at Fort Indiantown Gap (what kind of name is that?) in central Pennsylvania. Pretty safe except for the smoke from Canada's wild fires blotting out the midday sun. He does not have anything nice to say about the duty there. He was hoping for Germany.
