There is no criticsm of your choice held within this post
just my POV.

As a first reaction i couldn't be arsed reading through your role.
If i wanted to know your character motivations, having to read a long story and carefully select the lines that are actually relevant to me, would be murder (it also makes it harder to keep it in the mind when you're dealing with 2 or 3 people).

I don't know what imms think.

Story lines are nice, but tend to be imposing.

As a matter of interest, could you go back through your log and paste the lines you felt offered insight into your character?

-EDITED SECTION BELOW-
Ok i copy pasted the stuff i saw as relevant to your character and not window dressing..would you be able to insert the same info into a more concise form? (doing this copy/paste means i've read through the whole role now and it makes for a nice story - dunno about role, but nice story)

“Years of training and this is all I have to show for myself; a half-full purse and an inanimate bar mocking me.”
Current state of affairs

“Damned if I’ll sleep another night within the confines of these wretched walls,” he utters quietly, once again denouncing the mocking coincidence doled out by the dredges of civilization.
Curious - what coincidence doled out? He's sleeping in a bad hotel and has little money?

“Do I openly denounce myself, or society?” With a cynical snicker, he adds, “Surely, if suicide is my goal…my death the culmination of yet another foolish decision.”
Uhm, what made him start saying this? He complained about having a crappy bed, what's that to do with society?

“I am a weary wanderer, burdened by the monotony of predictability and expectation. I rest out the storm here because it suits me fine, and will find as much comfort here as I would anywhere else.”
Tells us why you'd rather sleep in a storm, than in a crappy bed

"Surely my ability as an assassin has no progressed to allow me such fame,” he offers with a snide smirk.
You'll freely admit to a stranger that your an assassin

“So much like your father, I can already see. You carry about with you the arrogant indifference he was so well known for amongst us.”
"Skeptical and cynical, yet I sense within you the unyielding spirit I found within your father. "
Personality info

“I can find no purpose to my life. I live only because it is what I know, and have felt empty my entire life. How can you know this?”
The crux of the Character

Rithlan interrupts him, quietly stating, “Yes. I think I do understand now. More so, I feel that this is somehow right. Like the last piece of a puzzle I could not finish, though even complete I cannot yet see everything that has been pieced together before me.”
Your character has suddenly discovered why he would want in sylvan

"a newfound strength of pure hatred"
He really really hates something

..a year later you go and kick the crap out of 9 orcs....(without reason)

As a matter of interest, it doesn't tell me why you'd kill a good aligned tribunal, your role told me why you cared little for society, not why you should go around killing folk who -are- part of society...