Re: Caboose painting advice

I've been around railway preservation for more than 30 years. However, I've not been directly in charge of any paint project. But, I may be able to offer some comments:
Treat or prime the wood well before painting. I have seen a number of well-intentioned paint jobs flake away because the wood was not primed. At our museum there is a wood box car painted a dozen years ago that prior to its repaint it got a test patch of primer and color overlapping. The one place on the car that the paint is not flaking is when the primer of this test was -- the painter of the complete car went direct to the wood without a primer!.
Make sure that your primer penetrates into your wood and bonds to it. Brush it if you have to. Thicker paint can also hid any weathered grain.
The comment about tracing your lettering before sanding is important. Sometimes you have to sand away recent paint to find the railroad lettering or even to document an older style of lettering. The artifact is the best resource. It can also supply the paint chips to match (on a passenger car or a caboose up under the end roof overhang is the best location to look for un-faded colors. I have heard railroad and carriage museum curators remark about getting calls from private owners who wonder what to paint, strip, letter their caboose or buggy after they had chemically stripped all the paint away and removed all trace of the original paint.
Brian Norden
member board of directors
Orange Empire Raiwlay Museum