Okay just a warning. My words down there will make me sound very mean. If you think so your wrong

I actually think this overall guild idea can really work and could be fun. I'm going to be picky about everything because I want you to be sucessful.

Just a friendly tip about your history...People tend to get 'iffy' when one decides to say their guild originated in some far away village that was/is secluded from the goverment, as in the Octarchy. The fact that your saying 'untamed wilderness', which is something I can not say does or doesn't exist in Yliakum, will not help your story. While I'm sure its best to avoid that part all together it would probably make a mess of the guild history you've assembled

Instead I say you should say you came from a 'settlement' inside the Stone labyrinths. Gives exuse for all the havoc, evil, etc as well as a reason for why you aren't able to return home. You left the labyrinths by death realm, as said in your history, and so finding your way from the entrance would be rather tricky.
- They had studied the tomes of Drakku, and learned to relish death's embrace.
You spelled Dakkru wrong up there but thats besides the point

I'm curious to whether your guild is relgiously alligned. In other words, is it a Dakkru only club or do they accept other religions? I'd say your guild would probably do better if you did claim it Dakkru alligned. Gives you reason to 'be evil' other than whats in the history. It also gives an actual In Character reason for others to join you. From what I get you seek revenge on your old village. I don't see a point to anyone else ICly joining you just to help you get revenge (though I'm sure people will find some kind of IC reason). Saying your Dakkru worshippers gives someone motive to join and even help with the whole revenge process.
You must know the advance techniques of individual combat, and have gained the respect of the people of Yliakum. At this level you will embrace the life and actions of a DW, and have the ability to award points and rank to those below you.
I've no problem with this except for the part about gaining respect from the people of Yliakum...Same happens in the Objective...Of course I could just be a little confused. Obviously all the evil, death, dark way, and 'blade for hire' stuff doesn't make you guys sound like the law abiding type. Yet your seeking respect from the regular citizens. So is the actual guild supposed to be secret then? All this stuff an undercover operation? If so thats not a bad thing, it just didn't come off clearly to me. Of course I might just be the silly one who didn't notice. If not and your 'in your face evil' I'd recommend not expecting anyone in Yliakum to respect you..Fear you maybe but not respect.