Let me play devils advocate here Rock....

Are you saying that a person sitting on the wing of the plane in your above scenario would feel 100MPH of wind hitting him in the face?

While sitting on the wing of that plane, he would look over his shoulder and see the observer standing there in the same position relative to his seat on the wing of the plane. The observer has no wind hitting him. His hair is not flowing in the wind. Is the person seated on the wing of this plane feeling his hair flowing back in the wind? Can we put a wind sock on that wing and observe a reaction to a 100MPH wind?

...........

Now take note... I am not taking a position any longer on this scenario. Those that argue that the plane would take off or rather should take off seem to be correct.

Also those that claim it may not take off have also offered some valid points and also seem to be correct. (I'm also not talking about those that bring the wheels or other matters of friction or groundspeed into the debate. The debate is beyond those aspects)

I have some further thoughts and questions on the subject, but it involves your answer to the above question I have asked. That answer would lead to further questions possibly regarding the effects of air viscosity and compressibility involved in this scenario. All of which are included in the NASA links and have a direct bearing on the entire subject.