Re your first point: I was imagining doing the two experiments separately. But even if you do them at the same time, as long as you don’t put the two objects right on top of each other, the earth’s acceleration would still be slanted toward the ball, making the ball hit the ground very very slightly sooner.
Re your second point: The object would be accelerating in the direction of earth. The 9.81m/s/s is with respect to an inertial reference frame (say the center of mass frame). The earth is also accelerating in the direction of the object at some acceleration with respect to the inertial reference frame.
Earth is in this case not an inertial reference frame. If you want to apply Newton’s second law you must go to an inertial reference frame. The 9.81m/s/s is relative to that frame, not to earth.