What color is in the room in the top photo, with the wainscoting? It looks gray to me. I have gray owl in my bathroom, and it is VERY cool and almost has a blue tint to it. Keep that in mind. Revere Pewter is a great warm gray.

Hillary, I am not a professional so I try to think of things that could be done by a homeowner on their own without spending a lot of money. If the grids in your doors cannot be painted then I would paint the door white. I would trim the tree so that the trunk is viable. Evaluate plants to determine if they should be relocated. It is not attractive to cover the lower windows. Plant something attractive and flowering near the door. Grow grass in the small bed at the end of the landing. The entrance will have a cleaner look with that bed gone. Any plants you choose for the center of the foundation should say low.

I like the current color combination. How about painting the posts and the trim around the windows white? Paint the shutters a color you like. I love this green called Lush with gray. I would paint the shutters Lush.

@Diana Bier Thank you for your input Diana and suggestions and fresh ideas. And @roarah thank you as well for the ideas. I have written to Houzz about why we cannot load photos. I wanted to show you all I did paint my open study off the foyer a very dark Van Duesen blue by BM but because my dining room was so dark before I used BM White Dove in it for a break but I do love dark walls and may paint again in the future. Maybe some dark velvet draperies would be pretty in the DR for drama or is that too much with white dove. My house is very open and the DR and study flank each side of the foyer as you enter the house with case openings. In the meantime I have a technical question for everyone. My dining room is 15'9" x 12'4". I was thinking I needed a 9x12 rug until I tried one and it is about 6" too wide. I will have to move my funiture to place it on top. uggg it is all so heavy but I want to do the right thing. So that leaves me to find a 8 foot to 8'6 x 12 or 13' rug which is not easy to find on the width. SHOULD I bite the bullet and go for a 10x14 for this size room and just move everything again - then the funiture would rest on top. Just wondering what is the right size for scale of room.