LOST Theories (will have spoliers)

[Jeritron]

Originally Posted by wwe2222 Hmmm I dont remember him on the plane EDIT: He was with Ben and Hurley. Im sure he sailed off the Island in his boat

Yea, I'm pretty sure he missed the flight. It doesn't matter too much though, since if he wants to go home Hurley can let that happen, and he obviously would.
Obviously he wants to go home and see Penny and his child, also. Widmore took him against his will to begin with.

That's really the beauty of Hurley running things. As they say, he can do things his way and you know you're going to get pure and fair intentions.
Ben staying is perfect, not only because The Island is his only home, but because he's such a morally ambiguous character like Lock Jaw said.
Serving Hurley is really part of his real life pennance. It's also great that he's welcome to move on in the afterlife with all of the other good characters, but chooses to think about his bad deeds for a while longer.