What do I do about the brown wood trim when I redo kitchen cabinets?

I have a 1927 Milwaukee Bungalow style home which is loaded with a lot of wood trim. I plan on painting my kitchen cabinets a dark gray and some of my wood trim runs up to the cabinets. Do I paint the wood trim around the cabinets or just leave them? My husband does not want to redo the oak woodwork and I think if I just painted the kitchen trim it would look tacky up to the dining room entrance, which is surrounded with wood trim.

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