Let me get my little assistant and we'll compare old (left)to new(right)...
$ vs Stack of Coins.
I initially mistook the pile of coins for oil drums/fuel. Even so, still superior to the dollar sign in my opinion. If the coins could appear less like drums though, that would be good. Add a third, very short pile of coins in front of all the stacks, and slightly to the left of the current center stack and that should dispel the similarity to drums.
Loafers vs Dress shoes.
About the same, no real change.
Fat binoculars vs skinner binoculars.
I almost prefer the old ones, but not a big difference.
Arrow over ruler vs crosshair over ruler.
I don't like this change, much prefer the old icon.
Daggers vs tanks.
Improvement, but I can improve it even more:
Dot vs man.
Man wins. Hence why dots are extinct, just like saber tooth tigers.
Block vs tank.
Tank wins, as we can see here.
Wings under vs aircraft inside.
Aircraft wins. Ever see a bird take on an airplane? No, Sean Connery from Indiana Jones doesn't count. That was a flock of birds, not just one.
http://www.youtube.com/watch?v=Nf1bx37lh_M
Swiggle under vs anchor inside.
I prefer the anchor instead of the symbol that represents 'approximately', but I'm not completely sold on an anchor being the best choice. It's better, but perhaps an actual ship silhouette would be even better?
Hard line under vs tank in shield.
Tank is pretty much a solid winner. Clearly conveys 'defense' and 'hard target'.
Wings under plane in shield.
Plane wins, same reason as tank in shield above.
Body armor vs infantry in shield.
I'm a little conflicted. The infantry is better, but I'm not sure that's the best infantry image to use. That posture looks like where you would find infantry in open terrain, running with gun up. Perhaps crouching(camping) would better represent close quarter combat. Or him being armed with a grenade or molotov instead of holding up a gun.
Posture more like the ones seen here:

Or

Or

Not the entire images of course, but the posture of the man with the grenade.