[@Vietmyke]Hopefully this addresses the issues. If not I can work on editing the CS. 

[hider]A lot of this is down to not explaining myself well. He isn’t a known figure amongst the peasantry and normal merchants of Holden, but rather amongst the criminal brotherhood of the city. I imagined them swapping stories about one another’s exploits in the darkened corners of dingy pubs, each trying to outdo the other with their daring and exploits. The ones who could actually back up this boasting with action would start to make a name for themselves. 

He’s not a reformed criminal, he’s a conflicted one. He doesn’t do the wrong things in life because he’s a bad guy with a complete lack of conscience, he does them because he sees them as the only recourse in the dark world he lives in. His mother was the best person he ever knew, and she died an undignified death. On the other hand Theron Kingmaker has spent a lifetime as a criminal, and now he’s arguably the most powerful man in the city of Holden. Roland’s witnessed good people be punished and the bad rewarded. He’d like to be a better man, and honour the lessons his mother strove to taught him, but he’s never been shown much reason to be good for goods on sake, and is frankly a little afraid of the personal consequences if he ever was.

The nickname was a placeholder from when I originally envisioned the character and began the CS. To be honest it doesn’t suit the man who has come out of the other end of the process. I’ll remove it.

Yeah, the guard captain was perhaps a push, but there are a few justifications I had in mind. Firstly, just because a man is corrupt doesn’t mean he’s a murderer, or is even capable of murder.  I figured he was given the job but proved to squeamish to do the job himself, and didn’t like the thought of giving the task to someone else in case word got back to Losthill that he’d proved incapable, and potentially be replaced in his position as ‘the inside man’ at the prison. As it’s a dark fantasy setting I imagined it was a crapsack world, and that the resources required to forge papers for a conscript would be relatively low, thanks to a combination of inept bureaucracy, general disinterest in the individual situations of the conscripts themselves, and a high need for ever increasing numbers of ‘demon fodder’ in the New World. If I’m wrong about the world state let me now and I can change it. Like you said, it’s a means to an end, but it’s not the only one I envisioned.

I left it out of the backstory as I was trying to present the idea that it’s a gift that he has been taking for granted. As a boy, he thought it was something everyone else was capable of, and as an adult he’s been using it for so long that it’s become intrinsically part of him. He can’t imagine life without it because he’s never even tried. Conversely though he’s never investigated into why he has this ability, never thought to approach a mage or scientist to help him find a reason to explain this strange phenomenon. I was partially trying to avert the whole “woe is me, why do I have these fantastic powers that make me different from everyone else” mindset, and thought it would be refreshing to see someone who just accepted his abilities as something that life has given him. He doesn’t think he’s cursed in this regard, nor does he think he’s gifted. He just is. 
 
Sorry for the lack of clarity, I'm not particularly fond of, nor good at CS's. I never present the information I have in my head concisely. I prefer to ease things like personality and history out over the duration of an RP, as the fluidity of that approach suits me better. 
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