Glock: Positive: barrel mounted closer to your hand and at a better angle to the grip (I think), no safety to fiddle around with, extremely reliable and always functions well out of the box, holds more bullets (unlikely to matter, but still), designed to be used and learned by anyone pretty well
Negative: wider pistol therefore harder to conceal, crappy trigger, ugly, sights are kind of huge and not that great,

Kimber: Positive: narrower (easier to conceal), better trigger pull, more attractive, cooler, 1911 style pistols are apparently the choice of Special Forces types who obviously know more about this than me, metal frame so you can pistol whip suckas without their laughing at you, lots of stuff to modify it with if you have some desire to do that.

Negative: has manual saftey, some people freaked out by visible cocked hammer (silly but true), barrel higher from hand, more felt recoil