Despite all these connections to New York, Jake and Roland are rarely there together in the books, so this picture seems to indicate an original scene.
Seeing Jake in New York might indicate that this version of him has not died.
Every world has a version of The Dark Tower, in our world it is a rose that grows in an abandoned lot in NYC.
When Jake and Roland meet in The Gunslinger it is because Jake died in our world, and found himself in Roland’s.