The current character I'm working on has (among other things) the Criminal SIN quality. The idea is that he's back on the street after a stint in prison, and he's being coerced into running by a crooked parole officer. I put together a basic cyberware package figuring that was the 'ware he'd picked up after being back on the street, but then I thought it might be interesting to play the character fresh out of prison and pick up his 'ware in play with whatever I could beg, borrow or steal. If he had 'ware before he went to prison and it was removed it would make sense he would be starting over with essence holes, but I'm not aware of any way to do that by the rules.
It seems like it would be a minor negative quality (magical healing would be more difficult), but once the character starts picking up 'ware there'd be no downside, the essence holes would just be filled up. On the other hand, instead of being able to just buy the pieces I want limited only by the chargen availability restrictions, I'd be limited to 'ware I could find on the street-- either by getting the availability rolls or by 'legging people with the gear. (This character wouldn't seek out people to steal cyberware from, but if he came across it in the course of doing business, he'd probably take it rather than leave it behind.) It certainly complicates the process of building the basic street sam.
I'm not really interested in creating a negative quality to cover it, but I wasn't sure how to handle a character like this without just handwaving it. Any thoughts?