Nox, your example has many failings.
But the most important one: If having an armed Joewolz in your country increases freedom, then, by all means, he oughta have a Stinger and a Antitank Gun too. You know those RPGs the Iraquis use really help them against Helicopters etc.
And especially Hand Grenades should be legalized, as they are of utmost importance to any insurrectionist and urban warfare.
All in all, Joewolz should be allowed to bear Handgrenades, at the very least.