I would paint the trim and refinish the doors.

Perhaps the first step is to look in the idea books you've made on Houzz and see if there's a pattern in what you've liked in the context of a room. If you look and see that the rooms you've added have white doors- you have your answer.

I have been up to my ears in paint lately and I know how much work is involved to paint everything yourself. If it were me and you like your existing trim as is or don't want to paint it, then I would consider painting the doors a nice Sherwin Williams or Benjamin Moore color that's neutral, light and compliments the color of natural wood trim and wall color. Maybe an Antique White, Alabaster, Dover White, etc. Good Luck! Post pics! :)

You can easily refinish your trim to better match the door which is beautiful and adds a lot of warmth and charm to your home.

White doors and trim always look crisp, and - to me - open up the room.

I'm normally for white doors but its a shame to paint those dooors.. I encourage you to look into look books first before making the plunge. Perhaps its a simple thing to paint the trims or walls to lighten up teh space.

Wood moves with changes in temperature and humidity. Wood doors have a lot of joints. The movement at the joints creates small cracks in the paint (see pic.) - so keeping the doors nice - and clean requires upkeep. You might be up for that or not.

If you like white, consider painting the trim white but leaving the doors wood. (see pic.)

Jhmarie- your point about moving joints is valid. I painted a sample door to see what it would look like and hold up (inside of a closet) before winter, and I noticed the cracking you are referring to.

You can replace your doors with white MDF pre-painted doors if you want less paint upkeep. MDF is more stable for movement, and sell your doors on craigslist or donate to the ReStore habitat for Humanity store - most every city has one. MDF will swell if it gets wet, so MDF doors need to be kept well sealed with paint. Personally, I like the wood with white trim look - I have it in my own home:)

Thank you so much for your opinions. While it will be more work, I think I like the idea of refinishing the doors rather than repaint. Here is one more expanded photo. Paint the wall paneling as well?

Your previous pictures didn't show any wood paneling, is this in everyroom? If the wall paneling is in one room only I would stain that room. You could paint the trim white and the panel section the same color as the walls.

I think you should paint the wall paneling the same color as the trim.

I'd paint all the doors and trim white. Oak and pine take stain very differently, and will not look uniform when stained. Painted trim indeed looks crisp against a contrasting wall color. Do you have wood floors? Stained wood floors would look great against painted trim.

The paneling shown is just in the family room and office (I plan on leaving it intact in the office for a richer feel).

Paint it.

I would also paint the trim and doors...Dover White is a nice color by Benjamin Moore, stain or semi gloss finish

Start within painting the trim. That will help a bunch.

We can't tell where the wainscot is, so can't help with that just yet. Is it in every room? Tell us more.

The wainscoting is just in the family room and office. At this point I plan on keeping the wainscoting stained in the office, but the family room is up for grabs. I think logic says that if I paint the trim, I should paint the wainscoting the same.

Not seeing everything and not knowing your taste or what is going on with everything else...I would suggest.
I would paint he trim & doors and refinish the floors
If you like white, extra white by SW is clean & nice very neutral
and the walls Antique White. Antique white is a warm color.
I just selected this combination for 190 garden homes. I think it works with so many different looks and feels good.
If white is to white Dover white is nice, just select a wall color a little deeper in your favorite tone.
The floor would look great in a warm medium tone. I used many times a formula of 1/3 of special walnut, mahogany and natural. Mahogany has red and walnut is brown and natural tones it down. I have also used 1/2 mahogany and 1// special walnut it depends on on dark or deep you want the floor.
I would suggest to buy a piece of unfinished flooring like you have and test it to achieve the color you like. Keep in mind your furniture color tones. Good luck!

Test painted door. Looks good so far. Will post more as we move forward.