What do new houses in your area have for trim and paint color combinations? You can do some armchair shopping if there are model homes shown in developments or if you look at new houses for sale online.

How old is your house?

following

Home is from 1926. Updated homes in my area mostly all have white trim and grey wall color.

If you want to keep the stained wood trims, use a white paint on the walls - not gray. It will lighten and brighten the room and coordinate with the wood without looking trendy. I think the window trim and door trim add character. I would keep them.

I recommend that you do an image search on Houzz using the term “dark wood trim.” You will be able to see how others have handled wood trim and get some good ideas for paint and decorating.

It's a lot of thick, heavy wood. I think just keeping the crown and the door molding would be enough.

for the baseboards/window trim, give it all a good sanding, ending w/a 220 grit. wipe it well to remove dust. prime w/something like Zinsser oil base primer, OR, you can use a good shellac. (shellac seals the wood so if anyone down the road wants to strip the paint off, the wood will remain unscathed under the shellac)

after primer, you'll prob want to fine sand w/220 or 320 just to knock down any nubs. wipe clean.

now paint w/a good wood trim paint. I like Advance from BM, or SW ProbClassic. use the white base right out of the can. it's very neutral w/no undertones. (or try Pure White or Simply White)

As for gray on the walls, your wood is warm, w/reddish tones. you'd have to pick the right gray.

But I think a white, or a soft blue or soft sage (blue or sage looks beautiful w/cherry wood) would look great.

I would likely paint the walls,the baseboards, and MAYBE the window trim the same shade,keeping the rest of the trim. Most grey shades will not show off that trim or floor, so https://samplize.com/. Which gray shade did you like? On my monitor, looks like BM Sea Pearl would be pretty but maybe too light for you.

Another thing to consider is using linen cafe curtains to allow more light. Designer Jeffrey Bilhuber seems to do this again and again. Can't work in every space, but maybe in yours?