Some very good points, I can add an addendum for his Days Gone after he drops off the radar. I've been feeling him out a bit more since writing him and there are some changes I want to make anyway - in particular, I think his attacks weren't communicated right; he's not meant to be an action hero, and the new unit working on his case file are intended to be working through cold cases. He's willing to work on Ops because he enjoys it, and he feels it's the only thing he can succeed in - and the heat on him isn't so hot, there's no active manhunt any more and he works under a false identity. 

I also think I'm going to reduce the influence his connections to his previous job. They're meant to be a pretty generic shadowy organisation who organise deaths for profit, and their reach is also meant to be fairly global, which means I don't want Jack to be too closely attached to them still so he's desperate enough to stay in Baltimore. He won't have any membership of the organisation any more, and he'll have cut all formal ties with them - his Arsenal will almost always come from something else, or more rarely there might be an incidental contact from his old job he has a favour from. This also means that another reason he has to go on ops and be in this cell is that he has lost his old lifestyle and job, along with its benefits, so this is also partially a way to keep living while staying in touch with the new world he's learned exists.

As for how he got involved with the supernatural and became a hunter to begin with, I'll cover it in more detail when I expand his Days Gone a bit, but it boils down to him having been issued a contract for someone who turned out to be involved in the supernatural themselves, who then survived his attempt as a result. He survived their reprisal by running and hiding, and then went on to do what he'd mostly always done by seeking out people who knew how to hunt the supernatural, so that he could do so himself.

I'm happy to make changes, ofc, but does this address your concerns so far?

Edit: I think I'm also gonna have him slip off government radar way earlier so that this is a real cold case. Their files will drop off very shortly after his pattern changes and he becomes more professional, to represent his shift towards a much more covert way of living, and I'll reduce the damage he did to them as well so there's a bit less heat on him.

[@DeadDrop]