I ride both Specialized and Cannondale and I LOVE my Cannondale Supersix... but in this scenario I think you'd be happier with the Tarmac. This is just my opinion, but a SRAM grouppo blows away the shimano stuff (yes, i've owed ultegras and 105s).
Don't worry about the year model, you're not compromising anything by getting the 2010. You're also getting a better price for the 2010.
Also, i agree with v70cat, check out the Scott CR1... if you want to save a little more cash and get the same components with probably better rims (comes with Ksyrium Elites i believe). its also very light.