huh... back when I had a pirate character we'd often work in small groups - myself and usually one other in a gunboat, someone in a VHF or larger capship, and someone in a transport to pick up loot when the enemy failed to pay up.
The other warships never participated in the pirating, though they were grouped - they were around to fight off the "liberty capwhores" if they showed up to spoil our fun =P
EDIT:
It never was very successful though. The fighter/capship pilots got bored because they couldnt get any decent money out of the pirating, and unless we attracted enough attention over systems chat for lawfuls to show up they really didnt get to do much.
That, and I was always demanding more rum than credits.