Okay, so after being pretty convinced that the Losties' lives in the alternate timeline are better because Jacob wasn't able to interfere in them, I'm beginning to doubt that this is true. When I shared this theory with my wife she raised a really interesting counter-argument: in the original timeline, the MIB might also have been interfering in their lives. Now, it seems pretty clear that the MIB is stuck on the island, so how could he have interfered in their lives, you ask? Well, it does seem that he has representatives or emissaries off the island. For example, Charles Widmore may be in league with the MIB, as evidenced by the fact that Bram warned Miles not to accept the job Widmore had offered him because he'd be playing for the wrong side.
So here's my new theory: the reason the Losties lives were all so screwed up wasn't because of Jacob's interference, it was because of MIB's interference (through Widmore and other off-island servants). I believe the MIB knew that they were the last group of Jacob's possible candidates and that he has been trying to make them irredeemably "broken" and to ruin them as candidates. And I believe that Jacob's appearances in their lives were not to manipulate them into coming to the island, but to work against what the MIB was trying to do to them; e.g. saving Sayid from being killed by Widmore's men when Nadia was killed, bringing Locke back to life after getting pushed out the window, encouraging Kate to "be good."
I have two major pieces of evidence for this theory:
1. We have several confirmed instances where Widmore or people who work for him have interfered in their lives. Abaddon (who works for Widmore) suggested the Walkabout to Locke as a spiritual experience, Abaddon tried to get Hurley to come with him to a "new facility", Widmore's men hit and killed Nadia, Widmore encouraged Locke to bring everyone back to the island, Widmore seemed to be ultimately responsible for both Faraday and Desmond coming to the island, etc. So we know for certain that Jacob isn't the only one who's been influencing their lives.
2. This is the big one: In the alternate timeline, all of the candidates are on flight 815 at the right place at the right time. So even without Jacob's influence, they all still would have been on that plane when Desmond failed to push the button and the plane was brought down. So Jacob didn't do anything to bring them to the island... they would have come regardless. Which leads me to conclude that he wasn't interfering in their lives to bring them to the island, it was for some other reason. And I think that reason was to reverse the damage that MIB was trying to do to them.
That's my theory and I'm sticking to it!