If you plan to replace all flooring with hardwood eventually I would suggest waiting and doing it all at the same time. The hardwood staggered joints need to flow into the adjoining rooms and not be cut at the doorways. If you are anxious to start you could come up with your plan and just replace your countertops now and start your painting. The countertops alone would help you feel you are making progress.

Yes, you want a good flow from room to room with the wood floors. Countertops would be a great start. Maybe a darker toned granite or quartz material.

Agree with the above. However, when you do get around to flooring, I think that you want to think less in terms of "matching" and more in terms of some contrast -- that is, the undertones of the woods need to be compatable, but you probably want your floors to be several shades darker or lighter than your cabinets so that everything doesn't just disappear into a monotone wash.

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Love the darker floors

I recently replaced the countertops in my kitchen and I have wood floors and cabinets:

This is the new countertop and sink. The backsplash is not in this picture:

https://www.houzz.com/photos/my-pics-work-in-progress-phvw-vp~54988842

The backsplash is partly in here:

https://www.houzz.com/photos/my-pics-work-in-progress-phvw-vp~56984150

We have the same wood floors throughout the main level - natural oak, similar to the pics above.