I would definately take the Glock 9mm and use that to get your first one (if I remember correctly there is no bag limit), that will build up your confidence and take off a lot of the pressure, then use the .45 and see how that goes.
Hopefully this will add enough fuel to the caliber wars to keep them interesting LOL
Although if you are going for surgical CNS shots calibers probably don't mean too much.
Its cool that Rich is so generous to offer up the challenge and use his own money for it!
And whatever you do,
Use the Force young Jedi...