The color of the gutters, windows and deck are similar to each other and very nice so I would find something in the same color range...simplify.

Where paint and color are concerned "timeless" isn't going to be a thing. As you are noting on your present home, things change. I've seem many homes like yours done dk. Dark like your garage doors.

The garage door color works really well so do that for all the things you want update The siding color you have is all wrong with the brick for sure. Landscaping is what will be needed for sure

If things need to be painted or repaired for sure do that from a maintenance perspective. That said, I fully agree, thos is a landscaping issue more than anything

Thank you! I appreciate all the feedback. Yes we are also working on landscaping but, after the siding is complete.

+1 to @tracefloyd recco to simplify where ever you can as it relates to paint - I’d want the siding to have a touch more grey to jibe with the brick - maybe SW tony taupe?

This is a large, elaborate house. Painting will be a big expense, so you may want to hire a color consultant who would come out to the house. In the meantime, I suggest removing the boxy foundation shrubs, then having the brick professionally pressure washed ("soft wash").

Please post an update when you are ready.

I’d keep it timeless by going with a warm off-white or soft greige for the siding, then a slightly darker tone on the trim for contrast. That’ll clean things up and feel more modern without fighting the brick and roof tones. Updating the gutters to match the trim also helps everything feel more cohesive.