I have already painted my rear grille bars and plan on painting the front bars separately also, then assembling the grille. I thought about masking after assembly, but that's going to be too much trouble, IMO.
As far as painting the lettering on the tailgate, they were not painted at the factory. I don't plan on painting my tailgate lettering.
One way of painting the lettering would be to paint the lettering color first, put vinyl letters on as masking (reverse of stencils), then spray your main color, then peel off the vinyl and spray your clear.