Gina appears to have been inserted into the Colonies at least "months" before the attack - and probably even longer, considering she seemed to be a lead for the Pegasus' refit program. Apparently the upgrade also proposed further increasing the automation of the ship, to boot, but then the attack came and the network was never refit.
Cain's objective appeared to be a guerrilla war against the Cylon occupying forces. What she really sought to accomplish, I'm not sure, because she'd eventually run out of fuel, ammunition, spare parts, etc.
Also, it looks like Starbuck's destiny might not be a good one.
EDIT: More musing, I wonder if Gina really cared for Cain (much as Caprica came to care for Baltar) ... also, not even the Twelve Colonies are safe from corporate buzzwords
