Hey, Boston-and-Maine, are those images of actual models or something photoshopped?
I'm curious as I've never seen anything like those before.
So, back to your question - I had to go check my references again.
Yes, the latest image showing something modeled after a NYC "standard" wood caboose, with the low-profile cupola, looks pretty close.
Some wood cabooses received plywood sheathing in later years - the only steel cabooses were the bay window cabooses.
The image of 18096 in the book shows the opposite side, but it looks like the paint scheme would fit what is in your image.
A few caveats:
The model sits much too high on the trucks. The trucks should be either U-frame or T-frame NYC caboose trucks with leaf springs.
The prototype 18096 was built in 1882 and was looking worse for wear when the photo was taken. It had angle braces attached between the body bolsters and roof line. They looked like either cable or truss rods with turnbuckles. That is probably a detail you don't care to model.
The stove chimney looks to be in the right place, but there is another vent or chimney on the model that should not be there.
Printed photos often exhibit strange color shifts, but the green color may be a little too deep. The three or four photos I have seen of green (not "Century Green"), safety slogan cabooses show what looks more like a softer, almost gray-green color. And, yes, black roofs and yellow safety appliances.
Looks like you are right in the "ballpark".
Modeling the NYC of the 1950s