How does dissolving a hydrate affect concentration? Say I have 0.72 grams of calcium chloride dihydrate. If I dissolve it in water, the 2 water molecules attached onto it dissociates just like the $\ce{Ca^{2+}}$ and $\ce{Cl-}$, right?

And if so, wouldn't it lower the concentration of the calcium chloride, as compared to making an anhydrous calcium chloride solution?
There are two methods to dissolve the calcium chloride salt.

For the first method you'd dissolve the salt in a "small" amount of water and dilute to some particular volume. So if the solution was 0.100 molar, the amount of water would be the same regardless if you started with $\ce{CaCl2}$ or $\ce{CaCl2\cdot2H2O}$. 

The other method would be to make say a 1.00 % solution by weight of the calcium chloride salt. Here it does matter. Do you want 1.00 % solution of $\ce{CaCl2}$ or a 1.00 % solution of $\ce{CaCl2\cdot2H2O}$?