Why, when the red flag is up doesn't the mail carrier get my outgoing mail. Also, why does the mail carrier constantly leave the door open to my mail box...letting the rain get on the mail?

A well trained carrier will pick up the mail when the flag is up and also close the door, Supervisor should be given a service talk to this bad manner mailman...

The only person that can really answer those questions is your carrier. I would complain at the office if speaking to the carrier doesn't work. We might have the same carrier- I ended up getting a locked box for the open box issue and when I have outgoing mail I drop it in the box at the post office.