I think if Jacob is revealed to be a real enough person, the writers will end up writing him a flashback that will answer most island questions.

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"How stupid are you Miles?" - Jack

As far as Dharma and island stuff Ben's flash back answered a lot of questions.
I think another Ben FB would answer even more.

I think smokey would get a FB before Jacob would.

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Doctor playing golf. Woo, boy howdy, now I've heard everything. What's next, cop eating a donut?

Libby's flashback! I'm at the edge of my seat waiting for that one.

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"Helen, do you remember that authentic Australian walkabout I told you about?"

either ben or christian

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I love my beautiful turnipheads...

I think if Richard had a flashback episode a lot of questions would be answered.

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I would really like to see a more recent flashback for Ben, like post-Dharma annihilation. We won't get that though, because it would answer too much of who he is and how much he really knows. I have a feeling that if we knew what he'd been up to around the time he began to raise Danielle as his own, there would be a lot told.