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I wondered why the Man in Black would kill Jake in his world to put him in the desert where he'd meet Roland. I still don't understand why, since at this point in the story, Roland has no trouble killing kids like during the battle in Tull but the Man in Black thought Roland'd come to love Jake. How did he predict that? Why did it work? That really puzzled me.
I think the Ma in Black can feel a lot and a lot of things. He's a powerfull wizard able to travel between the worlds, to see far away both in time and space and probably he could feel who might strike Roland's heart the way Susan did. The Man in Black seems to know Roland very well, the way an old friend would know what you might like.
Probably he wasn't sure who he was looking for when he walked through the whens and wheres, but he knew when he saw Jake. He knew that was the perfect bait for the trap he'd chosen: love.
But I think that Jake was first thought of as a whole by SK, then his story came. That's how things usually happen. First you see the character and then you build around him a lot of things to explain the way he is.
The Gunslinger is known for its incoherences, but I don't mind them. To me they're a great opportunity to feel and imagine how things are in this strange world. I love when things aren't said but implied, or even neglected. I can build my own vision, and in the case of the Gunslinger, it works very well.