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I've never tested how late you can manage to spawn him. It's possible the game stops checking after a while.
EDIT: Also, I guess the grapnel boost has to be onto a building rooftop; it won't work on something like a billboard.
He should spawn slightly before passing Grand Central Station. If he hasn't spawned by the time you reach the bridge, he probably won't spawn for you in that playthrough.
Checkpointing is sometimes one of those actions that shouldn't be rushed; make certain the game saves properly before quitting to desktop or menu. You can also set a checkpoint by entering an interior structure, wait for the save icon to stop spinning, then restart that checkpoint. You should then spawn from inside the new interior checkpoint.