Depends on culture. In my opinion, no.

It doesn't matter, you can still please a girl with a smaller penis. Average is between 3.5 -7 inches with 5-6 inches being most common

Doesn't matter, it depends on what the women prefers. Many prefer you to be natural, so maybe begin by trimming and then ask the girl if she wishes you to shave.

Doesnt matter, but I hear uncircumsized makes to woman feel better when engaging in intercourse

Tell him that he can get ready to enjoy the best night of his life!

Anything is fine. No good way to change it so why bother thinking about it.

Completely normal, let him continue. You might want to consider talking to him about to make him feel completely shameless about it. Encourage him to not close his door. Be open about it. In fact, I encourage you to give him your used panties