does the current siding need replaced? I think the shakes add charm, I would paint it a navy or dark green, maybe even gray

Great pics for ideas, thank you!

Yes, we are redoing all siding, front sliding door and windows with either KayCan or Hardieboard. We tried navy in the interior, decided we didn't love it, so went with black cabinetry.  So we are wanting to continue with black and grey on the exterior.

navy inside vs outside is different I will say that. boxed in it can look very dark but out side it can look very good.

here is gray

Super cool, I love that! And love the update on the window on top level 👌

You are very good, thank you!

https://pioneermillworks.com/shou-sugi-ban

Have you investigated charred wood siding, red windows and a silver/aluminium roof? This doesn't have the windows, but that's no biggie!