This clipping is the only reference I have found to the WN&P Traction Company thinking about expanding to Cuba. The plan does not appear to make economic sense as the main line of the Erie Railroad ran between Olean and Cuba and the Erie could meet any demand for passenger or freight service between the two places. The proposed route along Haskell Road did not pass through any towns of villages where there could be new customers.
*Olean, N. Y.-O. P. Brown, Olean, and associates are considering plans to build an electric railway between Olean and Cuba, via the Haskell Road. Rights-of-way have been secured and a report has been presented to the Western New York & Pennsylvania Traction Company, which has signified approval of the route.
Source: Electric Railway Journal, June 19, 1915, p. 1187, Google Books.