Notes:
Yes, the OOC comments will be cut down. I promise not to make any comments about Jess(who's 18, BTW, so it's not like I'm making lewd comments about a tween or anything, she's a year younger than I am)...unless RakeRon really leaves himself open for them.
The fact that Freeport isn't exactly a friendly place, but it's the only place you know of: You need to A) get out more, explore more of the world. It's a big wide world out there, you just haven't explored it; and B) Remember that you can sustain yourself out in the wilderness. Also, remember that Freeport is much more than just a Thieves Guild and a city of pirates. That's the reputation that it has outside of Freeport; think about what people say about New York, or even Iselin(our hometown), and then think about what it's like once you get there. A lot more depth.
Get Tak's motivation right, please. He's not so much pissed about losing the cities(which you can't be sure of, you just saw flames, chaos, and anarchy. You saw the aftereffects of rioting and death in Calvadia, and that's still standing) as losing his estate, his library, and his prototype designs for a magical Violet Wand. So really, it's more like "Kill the punks who messed up my books, my bed, and assorted paraphernilia for aforementioned bed."
As for attacking the Darkness? If you feel compelled, go for it. Just remember that your actions have repercussions.