Heh, I was thinking about what gangs look like, and the main picture that came to mind was teams of themed henchmen like in the 60s Batman TV show. Like with the Kings all wearing little crowns.
Anway, more seriously, it also made me think that maybe there could be different basic types of gangs you can hire.
You could have:
-Generic homies like we have now, without specific strengths or weaknesses.
-Mercenaries, good for guarding, sabotage and catacomb raids, but expensive to maintain, and lacking the subtelty to be effective at theft or kidnapping.
-Adventurers, like mercenaries but extra good for catacomb raids, and they absolutely won't do any actual crimes like kidnapping, theft or extortion.
-Collections of local hobos and other expendable rabble who aren't good for much but don't charge a lot of money and are easy to recruit back to maximum when they incur losses.
-Brigands and highwaymen, good at extortion, theft, kidnapping and other smash-and-grabs, but too cowardly to go into the catacombs and unskilled at defending your girls.
-Some sort of sneaky undercover rogue type, good at spying, theft and sabotage but crap at actual combat.