I have personally restored the roof on my Central Vermont wood caboose with Canvas. At the time I did the work I talked to a few Trolley folks to find out there best methods. The number one thing these Trolley folks stressed was the need to keep it undercover, and to paint it every year or two with a 50% thinned mixture of oil based paint and a product called Penatrol- Still available. I followed this advice as best I could but the car didn't live indoors even part of the year. the work was done about ten years ago and is now in need of complete replacement. I am currently contemplating a rubber roof job. I had resisted because of the desire to keep historical correct. however I cannot see doing the annual work (painting)which included removing the roofwalk and having to replace every ten years or so. BTW most Comercial roof coatings will cause the canvas to rot because they allow the canvas to retain moisture. I am not familiar with the rubber based material previously used on the C&TSRR but as Earl stated it is no longer available.
Al P.