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When you first make your gang, do you role for stat increases and skills? If so than how many times for ganger, heavies, and leader?

Also if I run out of manstopper ammo for a shotgun am I still able to use other ammo?

No to skills, yes to other ammo.

So does that mean that the experiance my gangers start out with is useless? If so why have any at all?

The points are already included in their base stats.
If you look at a Juve with 0 exp, compared to a Ganger, they have the appropriate stat increases.

You want to roll high for starting exp so it takes less time to hit the next bracket

But juves are still awesome to have because when they live long enough they end up being some of the best people in your gang. Thus making up for the crappy beginning stats.