Well done to Charles who gave the best answer to the last question. It was indeed Thomas Etholen Selfridge on 17 September 1908. The pilot was Wilber Wright, and it was a demonstration for the Army. See Charles' comment for more detail.
OK, this one is a little more obscure.
Question 3: Who and what. Who wrote this, and what was he writing about:
Under the best of conditions, flying a xxxxxxxxxxx was a "work-out". In bad weather, the pilot sometimes wondered who was in charge of affairs.