Adding interactive positions to organized crimes. 

• Master mind (already there)
• Get away driver (see additional suggesting that follows) 
• gunners
• explosive expert or safe cracker. 

Adding auto theft, cars could be stolen and sold on a market, similar to the drug market, different prices in different cities. Or they can get stored in garages (Which can be purchased in different cities, or could be an addition to Crew HQ's) and later used by the get away driver. 

Gunners would have a selection of 3-4 weapons

Same for equipment for explosive expert and safe crackers. 

Weapons and ammo rated on cost. Move expensive set used, the better the amount of money earned. Could implement to split percentage still in addition to the cost/rating of weapon/equipment

Cars would fall under the same, better the car, better the loot earned. 

Now I am just starting my programming adventure, so I don't know the work and coding behind this, but I have played a similar situation on a different game.   

No, where are these cars???

Cars could be stolen from HQ garage, with possible retaliation, like pickpocket/mug. Or from NPCs

I think the O.C that Izzy mentioned on IRC should be a Family O.C and not count as an O.C. This way there is more interaction and not random pick & choose that is current O.C formula.

With OP's idea, perhaps the Garage is like the armory where it costs credits to get one and random chance of getting a car or have to pay for cars. That way it's more of a money sink.

The Family/crew oc sounds sharp. Also if the car is used in OC take damage, costs to repair, funds allocated like HQ repair donations. 

Could we revisit this idea?