Boy am I at a loss on this one. According to Edson (see references) this road name existed from 1882-1885. Then the West Shore name was used. The West Shore existed from 1885-1886. I believe that when the New York Central & Hudson took over the West Shore there was a continuation of the "name form". This could be purely from greed. The local patrons liked some of their underdog lines. There are West Shore public timetables from the 1900s, so don't put too much in the name.

I have no further information on this maker. They have a distinct lettering style. They certainly didn't "crowd" the check with lettering. Note that the image shows identical lettering, when the strap check has lots of extra space (to accomodate larger lettering). The only assumption that can be made is that they were in business some time in the late 1800s. This maker is a tough one to find.
 

Stafford check

The N.Y. W.S.&B. Ry is the New York, West Shore and Buffalo Railway. This road  started as a competitor to the New York Central and was then taken over by the latter. Vanderbilt always had his way!. The image has been enlarged for clarity. Stafford made a huge distinction in size between the strap check and opassenger receipt.