In a craftsman home i would hesitate to paint ...a future buyer may prefer the wood finishes..as a buyer i would find the orange floor color more of a concern

I did simple white ben moore uppers and lowers surround and hale navy Island. I get lots of complements.

I don't think you can go wrong by painting the cabinets white, and Island gray. The question is, Do you want the cabinets white?, if so, do it. I think it hurts you only if the recoating/painting is done poorly. I have a kitchen almost the same as yours, changing from Maple to white cabinets, going to use Milesi coatings, so if her samples look anything like the finished product I expect, it was a no brainer for us. Our home does not have much natural light, we already changed to a white quartz counter top to white with light gray streaking and 3 x6 bright white subway tiles and wow has it made a difference.

Wood is coming back right now. I like the color and they match the flooring nicely. I think in a couple years this will be very desirable again. If you feel the need for change, I'd swap out the lights above the island for something with visual interest.

If this was my home I’d paint just the uppers and leave the lowers and island as is in the wood.

You might consider looking at these images of kitchens we have designed for clients. Note the fact that both cabinets are dark.

Echo Lake Modern · More Info

Lincoln Tower High Rise · More Info

If you really think that you will move in the next couple of years, I wouldn’t paint your cabinets. If it was me, I wouldn’t paint them even if I wasn’t moving in the next few years, but I understand that you may be tired of them and want a change. If you aren‘t set on selling in the relatively near future, you should do whatever makes you happy - as long as your friend is an experienced CABINET painter - not just an experienced painter.

Since your home is a PNW Craftsman I would not paint the cabs at all, much less paint them white. Maybe take a couple doors off to break up the sameness. And change the lights, hardware, and the chairs, and put down an art & crafts inspired rug if you want a new look. That said, if YOU love white and want white cabs, certainly go ahead and do it.

Painting the island only would be an option...