The major premise of this theory is that the sideways timeline is a "prologue" to the events we have seen in the first five seasons - it is not an "epilogue," nor will it be "merged" into the Island timeline. A major catastrophe or crisis will arise in the sideways timeline, and we will learn that the events of the original 5 seasons are the result of an attempt to avert that catastrophe/crisis.
So far, things in the sideways timeline have been rather quiet - all the drama has been in exploring characters' personal issues. This will soon change. There will be a tragedy or threat on a large scale, perhaps something like a nuclear war (which explains the drab, "funereal" color palette of the sideways stories). Our losties will learn, possibly from a messenger, that the only way to prevent this is to change the past. A plan will be hatched. Daniel Faraday, who figured out how to manipulate time via his research, may feature prominently. Some pivotal event will be changed, and that will flip us from the sideways world into the main timeline.
The catastrophe/crisis likely has to do with the DHARMA Initiative. We know that the DI made it to the Island in the sideways timeline (we saw the DI barracks underwater in "LA X"), and we know the Island sunk sometime after Ben and Roger left. My speculation is that the Dharmas, who came to the Island to study how to manipulate time and space, were successful in learning how to harness this energy. This was the catalyst for a crisis that has been unfolding slowly in the background. Maybe someone like Radzinsky figured out how to turn this knowledge into a weapon, and some group will try to use that weapon. Another possibility is that the Dharmas found Jughead (unexploded), took possession of it, and it got into the wrong hands. Or maybe they freed Smokey, and he's getting ready to touch off the Apocalypse.
So, the Losties in the sideways timeline will be offered the chance to undo these terrible events, but will have to give up the things that mean most to them. Ben will have to sacrifice Alex; Jack - his son; Sayid - Nadia; Claire - Aaron; Locke - Helen; Sawyer - Juliet; Hurley - his happiness; and pretty much everyone will need to give up their good relationships with their parents. Only by undergoing these tragic events will the Losties be able to bring about the necessary changes.
As to the "lynchpin" for switching one timeline to the other, my best guess is it has to do with Desmond's decision of whether or not to buy the engagement ring for Penny. In "Flashes Before Your Eyes," Hawking tells Des that if he buys the ring, "we're all dead." So, ring unbought, the chain plays out: Des doesn't marry Penny; he enters the race; he makes sure that the button is pressed until the exact moment when Oceanic 815 is overhead; his failure to press the button at that moment causes the crash; the Losties go through all sorts of temporal gymnastics that ultimately send them back in time; Sayid shoots Ben Linus; Ben is taken to the temple and healed, which eventually leads to him facilitating the murder of the Dharmas. If Des had bought the ring, Oceanic 815 would never have crashed, the Losties wouldn't have gone back in time, Ben wouldn't have helped wipe out the Dharmas, and the DI would have completed its work . . . leading to the tragedy that must be averted! .
This is why Hawking was so insistent that Des not buy the ring. She was part of the plan, and knew that Des held the key to averting the crisis.
In this theory, the Losties still have something they must do to ensure this all happens. I think they must, at a minimum, figure out how to send the message to the "sideways" timeline telling them what to do to change everything. Maybe they use Desmond as a messenger. Maybe this is only something the chosen "Candidate" for Jacob's job can do. But the poignancy will be, they will realize just how much heartache they are bringing on themselves as a result.
What about Jacob/Smokey? That's a major issue with this theory; they are largely on the sidelines. One possibility is that we've been conned all along by the writers. The Jacob/MiB rivalry ISN'T the key to the whole show, it's really about whether people are willing to sacrifice their own happiness to make things better for humanity. Jacob is the one who has faith that people will make the right decision and be able to go through with it. Smokey doesn't agree; he thinks people are inherently bad, and they are better off being wiped out by the catastrophe in the sideways timeline. So Smokey's promises to the "losties" are really that they can go back to that timeline - e.g., Nadia will still be alive! Claire can have Aaron! This version of events can be restored if the "message" is never sent to the sideways timeline. Jacob wants the catastrophe averted, but he can't bring this about directly; it has to be an act of free will. He can at most "nudge" things by giving! cryptic guidance, imbuing people with special powers, creating lists, finding the right "candidate" and guiding them to where s/he needs to be, trying to slow down Smokey by trapping him in the cabin with a ring of ash. But he can't tell anyone why he is doing what he is doing. He's willing to die for the cause, though: his own sacrifice for the greater good.
LIke most Lost theories, this one has more holes than a slice of Swiss cheese. The mechanics of the time jumps are a particular problem. If Des' decision about buying the ring is the key, I think the past has to be already changed by the time he makes the decision. If it isn't changed already, the Island is underwater, and there's no button to push. Lots of people think that the real pivotal event will turn out to be the detonation of Jughead, but that suffers from the same problem. The Losties arrived "back in time" before Jughead was detonated - so if the plan hadn't already "worked," how did they travel back in time in order to detonate the bomb? One can, perhaps, get around these problems if you accept that the main timeline has a "looplike" nature, and you can enter the loop at any point, simultaneously affecting both the future and the past. Still, I must admit that this theory is not obviously more "right" than, say, the "sideways as epilogue" view.
Let me know what you think, and if you have any suggestions that can improve the theory! Naturally, I am interested in the unspoilered perspective - I've been good about not looking.