"A few pieces of rolling stock"? "Individual numbers and letters"? Dry transfer vs. water slide?
IMHO, a no-brainer. Water slide. Charlie and Bob are spot on.
Plus, I don't know about your dexterity, but as I come to the end of my septuagenarian years, there's no hope/use for dry transfers on any of my projects from here to fire-drop.
If the choice is about the desire to have no, zip, nada residual film evident after the lettering and seal coat, I picked at that standard 'nit' loooong ago. Peace and tranquility are far more important than 'filmitis'. I've learned a lot from the forum on how to minimize decal film. I've lowered my own standards accordingly. (The LHS guys long ago gave me the alternative moniker "Lucas Gudinov")
But, that's just me. TEHO.
So, IIWM, faced with multiple cars of the same type as in your photo, I'd be looking for some custom water slide decal sets. The forum's Scenery Source List has several possible sources. I definitely wouldn't be looking to slide ONE letter or ONE digit at a time onto the model and keep everything set in proper spacing and alignment. I'd have the artwork all laid out properly...and then make appropriate cuts to accommodate surface features, such as standing ribs/shapes. Someday you might want to apply the same decals to less convoluted car side in a later effort...for which having the whole line...ELIZABETHPORT, f.i...intact would simplify the job.
FWIW, of course...
KD