We want to show some of the wood grain but we want to go for this darker color in as even a way as possible! 

Those who can sign up for the different programs get a badge/sticker with different metal colors.

you could do a brick step-out up top rather than a custom cornice that could be very pricey. it could look nice if you color match the vintage brick or go the opposite and do a contrasting color (like white to match your windows and basement) to make the top stand out. attached are some examples of some top step-outs. the brick mason doing the re-pointing could probably give you a quote for doing the top as well.

Im gonna use grout the color of coffee grounds.

another option may be to use finish screws. ( they are thinner than standard ) and you can use a color match crayon that matches your floor color to hide the hole.

Bigger plus for women of color.

Maybe a two color paint scheme.Am I on the right track?  

Should I remove the "Tudor" looking trim and just paint it all one color?

Leave the ceiling a different color.

I can control where my folders go and what color they are.This helps me to instantly visualize what is going on in my business as well as personal life.Total cost?