Thanks Bill and Dave for the input. I hadn't heard about ice and water shield, but I'm intrigued now. For my replacement roof, I too had put plywood over the top with the same thought in mind and will be using some new sheets on the re-roof as the old one's got a little water damaged and my drip-edge is taking up the top layer of plywood as I remove it.
I was going to put just an underlayment over the new plywood and roll roofing as the top layer, but considering now potentially adding another layer with the shield and then some boards over it. Not sure how much difference it will make visually to add some 1" boards net over the plywood, but I supposed one layer more of protection and more prototypical.
I can certainly sympathize with modern protection vs. accuracy concerns, although for something unseen, if it's not going to damage the artifact, I can't see faulting anyone over that - it just seems like the smart thing to do. 19th century car roofs were not the best design in the world - I have to credit the murphy roofs on the 3000's though. My 3693 doesn't have a single leak in the roof that I've ever seen and the only water that comes in is following the metal track of one side door down to the floor in one spot. Not bad.
Maybe they'll invent a spray paint that will look like wood grain to camouflage some ice shield on a stock car
Another question on roofing. I had put a very non-prototypical metal drip edge on my old roof, and it seems from what I can tell from other photos of the cars as well as some of the cabooses is that there is typically a small board about 1" square at the edge of the roof as the historical alternative. What's your take on how this typically keeps water away (or doesn't)?