[Seems like a good way to be led astray be the darkness if you ask him. Both Sauron and Morgoth could be terribly persuasive if you did not keep your wits sharp.]

Sure you're not. [Do you hear how much he believes you when you say that.] It's not the faction leaders that offers the quests, it's the people that live here. You merely use the funds you aquire to buy back your things from them.

Just be sure not to do so alone until you've upped your odds a bit. [Cause he'd feel a bit bad if Gadriel did something stupid and ended up dead for it.] ...It's not a competition and we, quite frankly, do not know why some people are sent back after some time.