I like what you have. I would NOT go darker.

Storm Grey looks good or Weathered Wood

Weathered wood is great look. But depends on paint color of exterior. If it leans brown/grey. Weathered wood best. If more redish Natural Wood good combo. Check samples at morning, noon and dusk.

If you haven’t already, request shingles in different shades and you’ll get a better sense once you hold up and can imagine the effect. This one is my favorite with the grey/brown undertones vs going too brown or too dark.

Ask your roofer to drop off the sample board. Look at different shingles on both sunny and cloudy days to get a sense of how they change.Weathered Wood, from the photos, could be the winner.

You house is beautiful!

I like what you have so try to go close to that