Stressing about matching wood colours shouldn't be a concern for anyone in my opinion! They look stunning together/ @Lars made the most important point here. If it DOES bother you, dress the table with more wood that doesn't match. It makes it intentional.

Yes - there will be a big rug. It’s coming this week so I plan to see how it looks once in there and will post a picture. Again, I don’t mind an eclectic look but want it to still go mix well and I’m also leaning towards the nightstands being too yellow.

How about the second floor where the new flooring will be next to the stairs? I would get more red oak and have the floor finisher match as best as possible or refinish it all and have it all finished exactly the same way.

@Skylar Ghrairi you are most welcome. I am trying to explain the why in all my responses because it's so frustrating to me to post a question and get strong opinions both directions but no explanation to help me decide. Someone doesn't like my design and says it's "awful" but even after I ask why it is awful I don't get an answer. I mean, if it's "awful" shouldn't the why be pretty easy?  The other thing I try to do is focus on the original question instead of mentioning a whole bunch of things the poster isn't interested in. Twice I've posted a question about materials and got my rooms redesigned. Argh!!!!! That's why I hired an architect! Hahaha... Still... I did make minor changes on the design for one of them, and the other isn't started yet, so I might yet change my design. I'm also trying to check spelling. 😁 Glad you feel good about your choice!