MPI,
A long gun will always beat a handgun. Greater accuracy, faster follow up shots(in most cases) greater capacity, greater barrier penetration and greater terminal effects. Unless the skill set is heavily slanted for the one with the handgun, the guy with the long gun will win.
What calibre is carried is a moot point. As a criminal planning an armoured car robbery, I could care less what they had strapped to their hip. at the end of the day it is only a handgun and level 3A soft armour will stop it. I see a revolver, I can confidently assume the security guard carries a maximum of 18 rounds, and will be slow to reload. If I see an auto I can safely assume that level 3a will still stop it and that the guard is most likely carrying 30 rounds. I'd avoid a handgun fight, that's far to fair. I'd show up with something centre fire. Like an AR or VZ58. Both defeat body armour which some guards wear overtly, not that it really matters. A night time hit would be to your benefit, as would a rifle mounted light. Fewer people out and about, fewer people to see what's going down or notice you and your partner(s) staging for the hit. Weapon light illuminates and blinds the guard as well as the custodian(that's the guy with the money). You remove the guard from the situation(disarm him preferably) and there is little chance the custodian carrying the money will draw his pistol, much less make an accurate dominant hand only double action shot before you swipe your selector to fire or slip your finger inside the trigger guard. he drops the money and moves his arms anywhere other than up, he gets shot. To be honest, it isn't worth dying for and no one I've met from any armoured car company would willingly die for someone else's money that is insured. If the bad guys wanted to kill you, they would have done it by now.
The windshield is not heavily armoured. I doubt it will stop centre fire rifle. More importantly, is the driver willing to take the chance and attempt to drive over a guy with a rifle trained on his head? Oh yeah, its standard policy for the driver to leave the scene if sh*t goes down. Again, I wouldn't hit the guards at the truck, I'd wait until they are out of sight so the driver cannot radio in the robbery. The truck isn't worth stealing because they're tracked by GPS(which is clearly marked on the outside the trucks). The guys who work the night shift are usually the new guys and may not know the neighbourhood all that well. Both major companies are union and the senior folks prefer to work days.
A hit during the colder months could mean the guards are wearing a toque which impedes their hearing, gloves which impedes their ability to draw and shoot. Their coat may cover their firearm(I've seen this many times). Cold weather means less daylight. Citizens generally close the curtains when its cold and dark, which aids the bad guys yet again. Oh and Christmas time means very large quantities of cash on hand.
All this and yet the calibre and make of their sidearm has nothing to do with how well I planned my fake attack. It takes brains and some forethought to be successful, not intimate knowledge of inconsequential equipment. The key is human nature.
TDC