That's quite cool, actually. I think the tag is definitely "New York Connecting Railroad", and the guy who lost it might have transfered to the LIRR at Jamaica? (It's still hell doing that today!) I don't believe the New York Connecting Railroad went out onto the Island like the LIRR, it's also interesting to note that the LIRR was taken over by the Pennsylvania Railroad around 1900, and a "connecting railroad" would probably have been obsolete by 1911 when the Pennsylvania Station opened in Manhattan, along with Alexander Cassatt's tunnels under the Hudson and East Rivers. I would say it's pre 1900, but what do I know?
Hope that helped,
- Teddy