Tates differ as demonstarted by some "L-o-v-e-i-n-g that trim when installed. For that reason I'd suggest you do what looks best to you, not what looks best to me or other Houzzers. It would be worthwhile to download an app that lets use different colors in pictures of your home. One thing to consider is early american,colonial ,traditional tranition which embraces abundance of natural wood.

Maybe consider a warm taupe that helps neutralize some of the orange tone of wood. Then add in decor elements that pull that color into the rest of the space like a rug in the bedroom.

Paint it white. It will be worth it.

I'd keep the pine for now, including the crown. The same wood runs through the windows, doors, baseboards and staircase, so painting only part of it white may make the remaining pieces look more orange and disconnected.

The cool gray walls are pushing the trim warmer. I'd test a warm off-white and a muted blue-green on large boards next to the wood. The blue-green bedroom photo already shows that the pine can look good when the wall color gives it some contrast. Keep the ceiling light, then repeat the wood with one or two simple pieces and use rugs or bedding to break up the amount of it. Live with the new wall color before deciding whether the trim still bothers you.

I’d paint it white - i am pretty frugal so would probably pay someone to tackle the downstairs and then I would do the upstairs one room at a time - fwiw I have gotten to where I almost enjoy painting, forcing myself not to rush and put on a podcast or let a favorite tv show play in the background

I dont mind the trim at all, and, I think its a good idea to remove the crown molding. Crown moldings do not work well on 8 ft ceilings, they make a room look choppy. If you end up wanting to paint all the trim, please paint it anything but white. White is so overdone these days.

I would paint it white. Classic look and goes with any wall color you might want to use.

I painted the stained trim in the first house we owned, so I've had to make this decision before.

I had the stained trim painted in my 1960"s home about 30 years ago never regretted it.

I like the trim to match the window so I would color match that white if you decide to paint

I'm wondering if in the bedrooms you painted the crown molding the same color as the walls in the different sheen and then the trim on those quarter circle windows to match the white of the window, the rest of the trim would look better.