I was sent the second and fourth photos by Jane Lunden, whose grandfather, T. Fred Dowling, formerly owned this diner. The barrel roofed model was replaced by a double ended Sterling Streamliner, possibly a secondhand diner from Connecticut. It stayed in the family through the 1960s, at which point it was sold. After that, it’s unclear what became of the diner, other than that the site is now home to car repair businesses.
The first photo is from the NYPL collections, and shows the barrel roof model in a different color scheme.
If anyone has any further information on this diner, its history, or when it was demolished, please contact me.