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I haven't read too many theories on what the loophole may be, but before too many wild speculations develop, what if it is not very complicated at all?
Only special people can request an audience with Jacob. So his Nemesis needed to find a way to get to take over the body/soul/image of the Leader of Jacob's followers. In all the years since the Black Rock arrived, he never had the opportunity to possess the Leader's "body" because they were never dead on the island. When the opportunity arrived and he was able to set up the scenario with Locke returning to the island dead (he is the one who told Richard to pass this info along), he jumped at it. Also, he wasn't able to kill Jacob on his own so he convinced Ben to do it (don't know why he can't do it himself), who was also one of the select people who would be able to see Jacob. Basically, I think the loophole was simply being able to use the right people at the right time. It just took a century or so to get the chance. Hope this makes sense...
Well, what do you think?