I have been reading alot of the theories on here lately and this seems to be something only a handfull have touched on.
We all know that MiB is trapped on the island and wants off but what if Jacob is in the same boat? At first I thought this couldnt be right but if you look at some of the details in the last 2 seasons it begins to make sence.
On the beach MiB tells Jacob "Do you have any idea how much I want to kill you?" He tells Jacob he will find a loophole, what if this is not his enemy telling his rival how much he hates him but his friend telling him how much he loves him and that he will save him from their curse. I think this is supported by the fact that Jacob told Hurley that he needs to bring Sayid to the temple. Jacob has been freed by his friend and now he is helping him to be freed also. He wants Sayid to be claimed by MiB.
I have been trying to think of what the MiB must do to be free, its obviously more than a case of just leaving the island or he would have done so already.
Perhaps he must be killed at the hands of a candidate whom has been claimed by him. When a candidate is claimed by MiB they lose their feelings and emotions. They hvave been claimed, I believe when you are claimed it simply means that that person is now able to kill you but if they do so they become Mib or Jacob depending on whom they murder
Jacobs loophole is he must be killed by a willing person whom has been claimed by him (remember young ben was healed in the temple? The spring would have been clear and that could mean Jacob has claimed him) This is Jacobs loophole but only the first part, because they need to leave together. Jacob now needs to ensure that the MiB is killed at the hands of someone claimed by MiB.
But I have another theory. The game doesnt end until both have replacements and MiB is not looking for his replacement.... his replacement has already been found in Ben, when ben killed Jacob he was made MiBs replacement. Once MiB finds jacobs replacement they will both finally be free.
You see to become Jacob you must be a follower of the MiB and have no emotions and yet kill him as it is the right thing to do and to become the Mib you must have been claimed by jacob and kill him of your own free will.
I think they are working together because they both want to "Go home". Yes Jacob can leave the island but he has been around for 100's of years. Perhaps when they finally find replacements they are sent back to their own time to their own families and can finally be human again. I cant see MiB meaning "go home" in that he simply wants off the island, these men are likely in their mid 30's and had familys that would have died a long time ago. Chances are they were tricked into becoming the protectors of the island themselves and have been looking for a way out ever since
I think that Desmond and Kelvins story in the Hatch was a play on this.... they are trying to trick people into replacing them.
I know their are a few holes in my theory but its my first post so be gentle ;)