Thank you for the replies and sewwhatsnew, thanks so much for the pics. That's really a pretty room, and although I've painted some of my cheap doors along with the trim before, I can see why you wouldn't want to paint yours. And it looks nice. Igloochic, my problem all started with my kitchen where I had to paint the window cause it didn't go with my dark cabs. Had to do dining room window too, since it is so totally present in the kitchen. Now that I'm about to change out the floors in kitchen and dining room, it's presented problems with the rest of the house. I won't even try to go into it here, it's just a big pain in the arse. I do appreciate your opinions....thanks again everyone.

LOL I figured photos would probably be needed, I'm not great at explanations. This is the hallway, the pic doesn't show all the doors, the darkness of the trim just really got to me after 5 years and the doors/door trim aren't in the greatest condition, the house was built in 1966, we are the second owners, most of the house is still in it's original built state. The trim and doors have a lot of scratches and poly drips from whoever originally finished them. The dining room area, after we installed and finished the hardwood floors, the floors have evened out a lot since this pic which I'm kind of sad about. What the windows look like up close. This is an old photo of the living room area after we moved in, you can see the size of the windows are really nice. This is a mock up of the living room/entry room space and shows sort of the built in plans between the two rooms that will serve as storage and separation in place of the common railing that is used in splits, most of the storage is on the entry side (which is how we wanted it) Built ins will be white with a wood top to match the floors. We're no longer going with the planks on the ceiling or all the way up the entry wall instead we're thinking a white thin depth coffered ceiling to hide the swirls (that I'm not a fan of) and wainscoting only in the small entry area underneath the built ins and around the front door going down the steps to the lower lever. Last two pics are the start of building the built ins. Two closed cabinets on each side with the middle one being open shelves.

What are you doing for ceiling colors? All ours are Buckram Binding and it does well with our dark woods. Our living room is Hubbard Squash and the LR windows face west. It's great. Our last house on Lex. Pkwy So. (Just south of Grand Ave) had 1 Portrait Tone bedroom, 1 Studio Green bedroom, Rembrandt Ruby and Strawberry Thief wallpaper in the DR. House sold in 9 days. The rest of the house used other of the AC colors. Glad you're hanging in there!

leave the doors,,,paint all of that trim white. all of it. replace the matching oak bar cart w/something else. consider replacing those wood look blinds/valance with some nice roman shades, or cellulars or woven wood blinds. those window treatments you have are severely dating that room as well as the oak.