Alright, decided it's probably easier to do it the long way because of the way BIS Arsenal exports classes.

In the init.sqf you'll need to put something like this

call compile preprocessFile "loadouts.sqf";

Then you'll need a file in the root of your mission folder called

loadouts.sqf

Inside that file you will put..

placeholder I'll finish that once you pass me the exported code for each class

Using the customGear.sqf file you made earlier, you'll need to switch the code to reflect this

private["_unit"];
_unit = _this select 0;

_loadout = [loadout_fnc_1,loadout_fnc_2,loadout_fnc_3,loadout_fnc_4,loadout_fnc_5,loadout_fnc_6,loadout_fnc_7,loadout_fnc_8,loadout_fnc_9,loadout_fnc_10,loadout_fnc_11,loadout_fnc_12] call BIS_fnc_selectRandom;

if (side _unit == east) then {
	//-- Remove unit's current gear
	RemoveAllWeapons _unit;
	{_unit removeMagazine _x} foreach (magazines _unit);
	removeUniform _unit;
	removeVest _unit;
	removeBackpack _unit;
	removeGoggles _unit;
	removeHeadGear _unit;
	removeAllAssignedItems _unit;
	//-- Call the randomly selected function to add the custom gear
	_unit call _loadout;
};

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Side note: I was in Chicago just a few weeks ago for work. Saw you were from Illinois.

Yeah I'm about two hours south of Chicago