Kim came up with a good theory that I can't take as my own. I asked her to post it, but apparently she would rather read Pride & Prejudice than blog about sci-fi dramas in her spare time. So I hacked into her account and will explain her thoughts as best as I can:
-JS
It is a mystery at this point what brings Sayid onto the plane after being so strongly against following Ben and his ideas earlier in the season. Kim believes that Ben, in his determination to get everyone on the flight, sold Sayid out on all the killings he committed. Who would have more evidence to give to officials than Ben? Sayid is now being extradited for his crime. This not only gets Sayid on the plane, but allows one of the former conditions to be present to help with "the crash" (the condition of Kate being extradited with detective-who-gets-his-leg-chopped-off-with-a-plane-part in season one). Sayid seems to willingly accept his fate to be taken on the Ajera flight as a choice to go back to the island instead of a life in jail.
What would get them on a that particular flight to Guam? Either Ben arranged with one of his people or connections to "extradite" Sayid on flight 316, or he is actually being extradited to Guam where he very well could have assassinated someone.
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