Things that are bugging me

I don't know if this has been brought up yet, and I'm too lazy to go through the hundreds of pages to find out. This is just stuff that's been bugging me and I can't shake.

-When Naomi parachuted onto the island, it sounded like a helicopter was malfunctioning and it crashed. If that were true, where did this helicopter(and pilot) come from? As far as I know, the freighter only had one chopper and one pilot-Frank.

-How in the hell did everybody get a picture of Des and Penny? After the pic was developed, Penny and Des went their separate ways, but Des kept the pic. WTF?

-If Horace is one of the main security guys, why does he have "Mathmetician" on his jumpsuit? Even Sawyer had a security patch.

-How did Tom end up in New York City to talk to Michael AFTER he was shot and killed by Sawyer? Probably something to do with time travel, but it's still wierd.

-Speaking of that: If you can't return to the island once you've left(according to Ben), why is everybody returning to the %$#@ island? Ben, Jacob, Jack, Sayid, Sun, Kate, Hurley, Miles, Charlotte, Ethan, Richard, and probably others left the island and came back.

-And finally: why is Jack so %$#@ annoying?

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