Any cycling specific short is going to be better than anything else, but the nicer (and unfortunately, more expensive) the short, the more comfortable and better quality it will be. Nicer shorts offer more panels, conformed construction, better stiching, and a more comfortale chamois. If you are looking for a recommendation, the Ibex and Smartwool shorts are my favorite for everything except the hottest summer days.

The OCR3W is a nice bike for fitness riding. Going to something at the $1200 price range will basically offer better componentry - so 10 spd instead of 8 spd, faster wheels, a stiffer bottom bracket. Not too sure on the Specialized line, but most manufacturers in that price range will offer both a more relaxed road bike (like the OCR) and a more race oriented bike, which will get you leaned over a little further forward with more agressive positioning. The frame itself is still aluminum and a carbon fork, so no major upgrades there. Basically better components and possibly different frame geometry.