As a general opening rule, 4th line stones operate for fast development on the side they're 4th line on (this extends to things like 3-4 stones, hence the side they are normally approached from - it's easy to make a lot of territory on the 4th line if your opponent leaves you alone to do it). Not only that, but a shimari, even loose, _really_ accentuates the importance of the side it faces. So, with a lower left shimari and a top right 4-4, the wedge seems relatively urgent.
$$Bcm1 Prisoners:

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$$ | . . d . . . . . . . . . . . . . . . . |
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$$ | . . c . . . . . . . . . . . . . X . . |
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- Click Here To Show Diagram Code
[go]$$Bcm1 Prisoners:

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$$ | . . d . . . . . . . . . . . . . . . . |
$$ | . . 7 , . . . . . , . . . . . , . . . |
$$ | . . c . . . . . . . . . . . . . X . . |
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I rejected "a" because, although it's a really big point I want, it doesn't feel quite as urgent as

to me. I rejected "b" because I wasn't happy about the development it allows White (something like this:)
$$Bcm1 Prisoners:

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$$ | . . . O . . . . . 9 . . . . . X . . . |
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$$ | . . . 8 . . . . . . . . . . . . . . . |
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$$ | . . 0 , a . . . . , . . . . . , . . . |
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$$ | . . . O . . . . . , . . . . . , . . . |
$$ | . . b . . . O . . . . . . . . X . . . |
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- Click Here To Show Diagram Code
[go]$$Bcm1 Prisoners:

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$$ | . . . O . . . . . 9 . . . . . X . . . |
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$$ | . . . 8 . . . . . . . . . . . . . . . |
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$$ | . . b . . . O . . . . . . . . X . . . |
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A move like "a" is now fairly urgent, and "b" still lives, but the whole situation feels like it's too easy for White to make points. That said, the approach is big too, and Black's development is fast and large, it just left me feeling uncomfortable. I have a bad feeling about the long knight's aji not being as "open" as my faster looking position, and I can see him cashing a lot more than me out of it.
I rejected "c" and "d" as places mainly through indecisiveness. I want to leave as much aji in the lower left corner as possible. I don't want him to fix the 3-3 invasion in sente, so by playing at

a possible approach at C8 doesn't look so nice, as the 3-3 lives unconditionally and he'll have to respond to my extension towards the top left. If he approaches from the other side, I extend along the left and he either has to reinforce or has some really awkward aji to clean up later. That's the hope anyway.