One problem here lies in how the Chummer generator handled licenses in the previous edition (haven't seen how the 5th ed version works). It did the 'one item, one license' method, and that can easily lead someone to believe that that is how it's 'intended' to be.
Well, that is kinda how it's supposed to work, if you get licenses.
If you purchase an Ares Predator, you have to get a license for it. If you specifically load APDS ammo, you need a separate license for that. If you want to carry it concealed, that's yet another separate license. So for you to walk into a secure facility with a concealed Predator loaded with APDS, you need to present 3x licenses if questioned.
Now the GM could say that you purchased a Pistol license, and you're allowed to carry several different pistols under that umbrella. Or maybe your APDS license covers your pistol, and your rifle, and your SMG. Or maybe your concealed carry authorizes your guns and your sword. If you stretch the rules a little like this, then players won't have to spend 1/2 their money on gear, and the other 1/2 on licenses for all that gear.
And as I said before, if your characters spend all their time in the Barrens, there's no real motivation to get licenses anyway. Which saves them money at the moment, but will make it very hard to do that job next week when they need to get into a downtown high rise.