Just wanted to put out there that I'm still highly interested! I'm hard leaning towards a thief now, as mentioned earlier.
My idea is basically every "organization' of Sk8ters has to have a branch of under-the-table acquisitions. These smuggled goods have to come from somewhere, right? Like every other role, these guys (which I'll refer to as Fingers until I or someone else comes up with a better term) tend to work alone and off the grid. Each Finger has their own methods and equipment, e.g. using Virtual Cloaking to hide themselves from cameras, hacking cameras within their closed network via Ocular App: Trojan, or disabling the power completely with some good old-fashioned breakers. Plus, there are usually specialized thieves. Grand Theft Auto, Vault Heist, Heir Honeypot.
Some thieves acquire more heat than others, but as long as they get the job done without implicating themselves or anyone else, then they will chalk it up as a success. Most, if not all, thieves dislike confrontation. This means that any job that involves directly interacting with live security or includes the intent to harm an individual as part of the objective are usually turned down. This does not mean they will not protect themselves when cornered, as they typically learn self-defense or carry a personal protection device.