You're replacing the "hall"

What about the bedrooms? Getting wood, or remaining carpet? How much cherry is on the first floor as it seems incongruous with the ceiling?

The fewer changes to flooring, the better, and you already have tile in the kitchen.....and where else?

For now, the bedrooms will stay in that carpet color. That cherry flooring and tile are throughout the 1st floor. It's hard to find an exact match to the first floor, and I'm nervous the cherry will look odd against the oak trim along the railing and stairs.

For now.........that's the problem with flooring decisions. It leads to problems up the road.

Get the carpet, all of it, thoroughly cleaned and delay this project.

Think about how long you will be in the house, as that matters as well.

The brutal truth is few want carpet edge to edge anywhere anymore. The broadloom industry, especially at the upper end, has responded with broadloom, whose most successful installation is a custom area rug.

Engineered products CAN be discontinued, and at that point if it should happen....you'd do what in the bedrooms.

The majority of oak trim, which seems to be doors could be painted. But? I'd delay until the entirety could be done: ) even if it is done in oak.

If you can delay your project and save up money to replace all flooring so that it is consistent throughout your house I would suggest that.

I see painted trim and pine doors in your picture. Railings look like birch to me as well. I see no hint if oak anywhere. Where is the oak you are speaking of? Hardwood everywhere upstairs (site finished), get a wood that is readily available and then save like hell so the downstairs can be matched as soon as you can.

I only see oak under the balusters along the part of the hallway that is open to the foyer (or whatever room) on the first floor (not sure what that piece is called). Unless the wood showing on the sides of the stairs treads is oak)