If MIB can't stand technology he won't be happy on either an airplane or a sub. He doesn't like sonic fences, so sonar isn't good for him. The island's electromagnetic energy might be what binds him to the island. I hope we get an explanation soon.
Without reading through all I think you summed it up. But the funny thing is we do not know how Jacob got around to see other folks off the island. Does he just show up? I was giving the electromagnetic pockets a thought as I think they hold significance to what is going to happen in the episodes to come for MIB. Widmore's team is hellbent on this subject enough to get Jin over to explain.
And I think we do know the answer if you think about this because one when Dr. Chang was having the Orchid built, they were drilling and came dangerously close to the donkey wheel. It caused the nose bleed and the drill was ruined. So we also know that thirty years later the same site held a chamber to help transport items and we know that Ben destroyed that chamber in order to get to the donkey wheel.
Which is all very interesting because we know Widmore was watching that area in Tunisia, knowing it was an outlet from the island. So the reality is that if they know where all of these pockets are they can stop folks from leaving through them. The trouble is that does MIB know about these pockets/loopholes? Something tells me that MIB is so focused on himself that he misses the forest for the trees.
So back to the question I don't think that Ben's original comment holds much creedence since he couldn't speak to Jacob. Second he knew that whatever was in there did not like the light per se. So at the end of the day you could say they do not like the modern torches. But to "hate" technology. I think the sonar fences prevent Smokey from entering for whatever physicaly reasons. Additionally it keeps out other people that the do not want to enter that area.
Widmore also was very involved with Dharma, if this is n't proving it then I am not sure what else will cause he sure nows what needs to be done to get things where he wantes them. now with that said if he believes that MIB was a compilation of stories and camp fire tales, well is he really there for a war with MIB?