Bought new to replace an '01 2wd Crew Cab SE which was a great truck. I was moving to the Midwest and wanted 4wd. Great advances since then, better in all aspects to the '01. Great motor with acceptable mileage for a truck. I get about 15-16 city, 21+ highway. Some folks don't like the interior, but I don't mind the plastic. It's put together well, and easy to keep clean. Gauges/controls are clear/logically ordered. Sound quality of speakers is good. I primarily an iPod via the aux jack. There is an iPod interface on the 2008s. Get that instead of the disc changer if you can. You might want to consider step rails as it's relatively high off the ground.
Powerful motor. Sure footedness of 4wd w/ traction control in the winter, but you'll still want sandbags. Styling. Overall quality, fit and finish. Sound quality of the speakers / sub woofer. Moveable tie downs in bed. Power sunroof. Trip computer on the odometer. Lots of storage.
Just make the traction control and side airbags standard already. It was a pain to find TC, and I compromised by not getting side air bags. Make some LE convenience options available (heated ext mirrors). Lockable exterior storage like in the Ridgeline. Man, the air filter is hard to replace.