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Is there a practical difference between light and dark brown sugar? I ask b/c I've seen many recipes specify one or the other. Do they really behave differently in some way?

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They have a different ratio of white sugar to molasses.

Therefore, dark brown sugar is more hygroscopic, and will have a deeper molasses flavor (and color, obviously) They're pretty similar, and you can usually get away with replacing one with the other, but if you want subtle flavors coming through, dark brown sugar might mask it.

I've seen recommendations that call for substituting light brown sugar with a 50/50 mix of white sugar and dark brown; I don't know how messy (or if even possible) to add molasses to light brwn to get dark brown sugar.

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Hygroscopic strikes again! – Ocaasi Aug 14 '10 at 3:05
p.s. why would having more molasses make it hygroscopic, I thought that meant water-seeking. Wouldn't the drier ingredient absorb more water? – Ocaasi Aug 14 '10 at 3:06
@Ocaasi : I'd assume it has to do with specific chemical bonds; both honey and molasses are more hygroscopic than white sugar, at least in baked goods. (I'm not sure if that's true before they've been cooked into something). – Joe Aug 14 '10 at 3:23
Yes, you can add molasses to light brown sugar to achieve a darker brown sugar, and you can even add molasses to white sugar to make any desired darkness of brown sugar. Just add the molasses slowly to the sugar in a bowl, and keep mixing until the color is homogenous (and is what you desire). – kevins Aug 14 '10 at 15:09
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If the brown sugar is being creamed with fat it's not even necessary to first mix the white sugar and molasses together...just dump in all together. – Darin Sehnert Aug 15 '10 at 3:20
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Oddly, most brown sugar on the market isn't less processed sugar (like many believe) but rather refined white sugar with molasses re-added to it.

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