In my opinion, contrasting color in cabinets and countertops look best only in very large kitchens. From what I can tell, your kitchen is not extremely large. So, I would keep as many of the elements the same, as possible.

I realize this is a current trend, but it will pass.

Are you keeping the black appliances? If so, I would paint all in the lighter gray.
Are you changing the flooring? IMO, the beige floor tone (on my screen) just don’t cut it with the cool gray color on island or cabinet painting whether you go light or dark.

confusing. if the existing cabs dont require painting i'd leave them. I would pick the island in as dark a gray as you can endure if it's gray you want. the reason is the floor...a darker contrasting island would be better. The counter would be better replaced in all spots with a white or whitish selection. So dont paint/go ahead and contrast with island cabinets and run continuous light counter throughout....... but if you are redoing floor that will be a different ball game.

Valinta - yes the Black Stainless Steel Appliances are NEW so they will be staying

Also, the flooring will be replaced with Acacia Hardwood.

Herbflavor - thanks for your input, mych appreciated. The picture reflects the new island color/countertop which we have just installed.

The flooring will be replaced with Acacia Hardwood flooring.

if you could put up even a sample of the floor that is going in it would be helpful if you want feedback on colors/tones/surfaces/etc.

Yes to posting a pic with the new floor sample in the shot. Also, how are you addressing the hardware on the island (how it relates to or contrasts the existing perimeter).

Paint all cabinets to match