RE: Clockwork
Thinking about it, I can understand reasons why the writers would keep him around: in case of a Devil's Advocate perspective, to show that Jackpointers aren't entirely Nice/Good Guys, and as an easy go-to source of internal conflict. Then, for occasional catharsis, he'll get temporarily banned and/or dumpshocked. From a rules mechanics standpoint, hasn't the guy been around for an edition or two? Plus, he's the sort to happily take "Low Karma/High Money" runs, so, sure, he's good at two of the most expensive niches at once.
Even still, the fact that this guy has harassed mods and their family on multiple occasions and has never been lethally double-crossed in a run strains credulity at times.
Also, looking back, JackPoint has invited new people on at certain points of most rulebooks, even if it is just to introduce new rules sections. So I don't really mind how it's gone.