I will write a few thing about how we can give "job" to the crew.
We should first having a "class" system for goons specialities, like Monaco, GTA 5 and, somewhat, Payday.

1) The Wheelman (in game: Joey/Pink B)

Melee Attack: Average
Gun Acuracy: Average
Hit Point: Average
Speed: Average

The Wheelman is your average gangster.
His most quality is that he can stole a car and escape faster.
Not being the most usefull class, it will be required for car stealing heist (IG: The Getaway Van) and joint heist, where there is a lot of people/security (IG: Jewel Store, BB Bank, Horseplay, Art Galley)

2) The Safecracker (IG: Gregory/Slick Jones)

M A: weak (or average?)
G A: poor (or average?)
H P: low (or average?)
S: Average (or fast?)

The Safecracker is your most valuable man.
Able to open/close door faster, use lockpick, and tools for safe (we should make that safes need a code/key to be open), can defuse and refuse a fusebox (so, using a fusebox like an switch) and cut alarm and telephone line (we should add alarm device and telephone box).
With the the Bomber, he is the only one who can use a bomb (when a safecraker use a bombe, it will be a time bomb).
This is THE MAN that open the way, but keep an eye on it, since he is really weak and precious.

3) Gunner (IG: Melissa/Stella)

M A: average
G A: High
H P: low (or average?)
S: fast (or average?)

The Gunner is here to clean the place and keep the crowd on control.
Fast. Accurate. The Gunner should have a biger and wider blue cone of threatening.
Another add, th Gunner should be able to use 2 pistol in the same time (so, having 2 pistols will send them in the same inventory place, use 2 times more bullet for 2 times more damage, when droped, both gun are on the floor).
Sheeps need to be guarded, as witness need to be watched.

4) Spy (IG: Cramer/Brandon)

Melee Attack: Average
Gun Acuracy: Average
Hit Point: Average
Speed: Average

The spy can use a guard or an clerk outfit to look inside the place, take some important thing like keys.
The only one thing to add will be more outfit in fact.
Like more security guard company (there is a "Blue" one, but we could add a Red, Green etc).
Outfit can be bought on black market or find (blue guard outfit in the BB Bank)
Also, this trai couldn't be used on some heist (for exemple, Benny's Bar, since the only guard is his cousin... maybe we should chan his color, grey/black, and make it a non unlockable outfit).