I'd probably go for someone learning to be a criminal, learning how things unfold and see where their path leads them. Usually total annihilation, but hey, it's all fun and games! 

i think the learning with rank and things getting harder and harder and the physical, mental approach to errors in learning, excitement, fear give an interesting range of emotions and attitude to go through as well as the worry if it all goes wrong what will the boss do.   I think the more as a trainee as such of the criminal world would feel the better in my case.   It also would give far more to write about in a RP

I've created characters that were virgin to the life of crime. I've created characters that were pros. My most consistent character development regarding the criminal aspect would be having the character fall into a gray area. Where they aren't exactly innocent, but at the same time are new to the mafia world. A small town or small time criminal. To me, having a criminal join the mafia is making them a career criminal. 

I typically pick characters that are new to the life of crime, often entering it out of desperation or nowhere else to go but a few times it's to carry on a family name or tradition. 

In role play I would think everyone has a level of experience in the crimminal world or we would not be meeting them.

From scratch, having the chance to form your character on the way is fun