I have never played an Operator, but I did design one as my next character in case of death, and this is my view:
As a discrete entity, the Operator isn't that interesting. What makes him interesting, to me, is his crew. Sure, Choppers get their gang, a Hocus has his cult, but a Chopper's gang are all pretty much the same - a bunch of hard dudes and a Hocus's cult, by definition, have shared beliefs. What makes an Operator's crew interesting is that they, to me, would be a mix of individuals, with a mix of skills, who rely on each other, but don't necessarily have anything in common beyond a need for barter. When I was designing Waters, my Operator, I spent far more time on the personalities of the crew. I literally made a matrix of what each person thought of everyone else, absolutely chock-full of plot hooks for the MC.
The one part of the Operator himself which really sings to me is this: to munchkin him the most (if I read the rules right), you need to be a complete douche.
You have sex with someone, getting you an obligation gig. This gets you +1 juggling, so you can do an extra job in downtime. But this is only a benefit if you don't spend the extra juggling attending to the obligation. So, you want to actually spend as little time as possible actually maintaining the relationship, so you don't work it and you let them down in some small way. Again. And Again. And Again. Only working the gig when you have to. Sure, they'll break up sooner rather than later, but in the meantime you're up loads of Barter. It's even better if you can juggle two or more relationships at once.
It's no coincidence that Waters had a long history of running from problems. It's like Chroma said - they are the biggest trouble magnets in the book.