Need help putting down new HW floor in 1800s house

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WT21

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I've got a mid-1800s house - fancy woodwork, uneven floors. This is a house I rent out, so looking for affordable, though decent quality.

The floor is currently two layers - thick pine boards perpendicular to the joists with an overlay of 3/8" 2" wide maple T&G on top of that. The pine runs east west and the maple north south. I'd like to put new oak down - 3 1/4".

My flooring contractor is suggesting to put the oak over the existing maple. One of the reasons being is the maple runs underneath the trim work and he doesn't want to fuss with pulling it up. Also would add another layer between the field stone foundation and the flooring.

So questions:
1. Do you agree that we could safely put the oak down over the maiple? Maple is super hard and I'm thinking it will split easily and the nail might end up in a gap between the pine boards.
2. Can we run the oak in the same north south direction as the maple? The flooring really wants to be north-south because of the room layout and where there are some humps on the floor (riding over them instead of along the humps). Is this OK?
3. I did think of putting down more plywood over the maple first, but then we'd have to trim every door.

So, are we OK putting oak over maple and can we run them in the same orientation or do I really need to pull the maple?

I did look at laminate and engineered products, but with the unevenness, I'm nervous about them failing, and I don't like the LVP options.

Any help/thoughts appreciated.
 
You either pull the maple, which means pulling the base, or you cut your doors is what I’m thinkin. Cutting doors is easy especially if they’re already pulled during the installation and don’t you already have to pull the base for an install, or would you just raise the shoe molding up without touching the base.
 
You either pull the maple, which means pulling the base, or you cut your doors is what I’m thinkin. Cutting doors is easy especially if they’re already pulled during the installation and don’t you already have to pull the base for an install, or would you just raise the shoe molding up without touching the base.
There is no shoe molding as of this time, so we would add shoe and paint to match.
 

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