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.
You said the two objects accelerate at the same rate, but then in the PS you said the feather gets accelerated faster. What do you mean?
Are you saying the feather gets pulled on more because the mass of earth minus feather is greater than the mass of earth minus ball? You would be right. If you lift the feather, measure how long it takes to fall, then lift the ball and measure, you should get the same number. This meme was assuming you either let them fall side by side, or measure them separately but each time conjure the object out of thin air.