One thing we have noticed is that if you start with only one territory it's really hard to progress as everyone is very poor and the tendency is to conquer other players' territories. This usually leads to a few squirmises fought to the last man obliterating all gangs but one (usually weakened). The option to generate a new territory is there but stealing from others is just better.
As a simple solution to this, I think that starting with more territories could help. This way, you aren't that bad if you lose one, everyone starts wealthier and that gives more options.