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Here's idea to give PC'S a sense of progress.
Each time a game event affects a gang, it takes damage points Maybe 1 point per gangster imprisoned or killed, 1d6 per captain/crew chief/special character captured or killed, 2d6 for the boss getting captured or killed.
Maybe the gang can heal 2d6 if the PC'S fail to prevent them pulling off a big score.
When a gang reaches 100 damage it has to roll on a Morale effects table, possibly even disbanding. It rolls again at each 50 points of damage.
Sounds good, but I'm cool with this being squishy. Also, I'm not convinced that all gangs are created equal. IMHO, the FREE MEN aren't as good as the Wound Ravens at extortion, but if a heist has to happen the FREE MEN are better at doing that. There is an M.O. to a lot of these groups that we should be aware of. Here's an idea. Let's call the hit points like a “Percentage”. Rather than rolling randomly, let's just decide how many “kingpins” or even how many adventures it takes to bring one of these down a peg, or down for good.
NEW IDEA: instead of hit points, why don't we rate a gang's power by how many districts they have? It is true that not all districts are created equally. However, we should be able to allow PCs to clear a single district in one or two game sessions. That should be the bar in my opinion. Want to take out a gang? Clear that district.