IMO i would leave all the wood trim, its gorgeous, and lighten up the spaces in a different way... warm white paint on the drywall, change out the dining chairs perhaps to fabric, not wood, add more lighting.

Here are Joanna Gains some ideas

https://www.hgtv.com/shows/fixer-upper/fixer-upper-style--shiplap-decorating-ideas-pictures

Lighten up the dining room by selectively pruning the shrubs blocking the window. Then add more lighting such floor uplights ($20 from amazon) in the corners.

Lighten up the living room by adding white slipcovers to the dark chair or by pruning outside the windows.

I would leave the trim the color it is too, however, what is very jarring to my eye is that thin strip of moulding high on the wall. It chops that wall up, rather than letting the eye move all the way to the ceiling. I would definitely remove that and fill in the nail holes, and paint. The wainscotting is beautiful.

What white paint colors are you considering? I also have wood trim (mine is darker than yours) that I am planning to keep but would like up update by creating more contrast with a white or slightly off white paint.

The wood trim is beautiful and gives character and texture to your house. I'm with everyone else suggesting that you use paint and tweaks on your lighting, art work, and furnishings to lighten the spaces. Here's an article on Houzz about paints that go with wood trim--not all of them are white. Many warm colors complement wood trim--oranges, turquoise and other blues,, cream

https://www.pinterest.com/pin/346214290074417244/

For reference, I have a wood trim Ideabook with some examples from Houzz:

NE 27th Whole House Remodel · More Info

Midcentury Living Room · More Info

Tudor revival · More Info

I would not paint the wood. That is craftsman style and looks very nice. Please do not muck it up like Joanna Gaines image that will destroy the value of the home. You could use some window treatments in white or cream.