Last February, a couple other 14er friends and I tried Gray's and turned back nearly on top of the summit because of blustery ice cold conditions (TR here: http://www.14ers.com/php14ers/tripreport.php?trip=9634&parmuser=alanonymous&cpgm=tripuser) It's amazing the difference angry winter and happy summer have... This was a redemption trip! And I took along a friend who (along with his pup Ginger) summitted his and her first ever 14er, and then promptly smoked a cigarette on the summit.
Conditions were perfect for late summer, early fall. The clouds didn't really move in until we were ~halfway down the mountain.
Road conditions: We took a Honda CRV to the actual trailhead with no problem at all. There was one section with a big ditch that a lot of people weren't willing to try, but once we made it to the top, we saw beamers, honda civics, etc parked, so they all obviously made it with no problem. Just be careful driving up the road and you should be fine, even in a 2WD car.
He was saving this the whole way up!