And I don't see why its a bad thing for the outlaws to work together and help each other out we are all outcast together not all of have necessarily broke laws but have been cast out by society for not fitting and following all the rules or meeting all the high standards
Like I said, if your objective is to form an outcast society, than you are certainly heading the right way! I think it'll be very interesting.
However if your objective is to have a successful criminal organization, I doubt it'll work much like that because crime will come at an expense, since you have an economic division to protect. This means that the military will spark enemy reactions and then have to not only protect themselves, but protect everyone else.
One of the flaws I think the structure suffers from is the emphasis of an Intelligence division. While intelligence is required, I think it is, like magic, just an addition to the outlaws and not a sector as important as Economy or Military (meaning it can be included in one or both of these.) Having Intelligence as a division means that you'll have a hierarchic chain in this division, which means having several members within... In an outlaw society I can't see these people being too useful, unless they are also working on the economy or military divisions.
To this effect I'd separate the guild into "Active" and "Passive" (Society, Guerilla; Collectors, Contenders; etc.) further simplifying the structure and not wasting a whole division on intelligence.
A 3 level hierarchy sounds best for both divisions: Guerilla would have base ranks like Marauder, Renegade (Mage) and Rogue (spy, thief, assassin), then a superior rank for each (respectively Ringleader, Heretic and Agent) and then a top rank for the council of leaders you usually have.
I think that in the field the most probable situations will either require no direct leadership or will require only one member leading a small squad. This makes this simple hierarchic structure close to the best.
You'd do the same for the Society part: Auctioneer (searches for merchants, prices, while also dealing with auctions and stuff), Collector (mines, hunts) and Craftsman (smelts, smiths, etc.) then the next level of, respectively, Dealer, Foreman and Artisan then the council.
This way your intelligence is divided into two divisions making spying harder for enemies (if it's divided into two guilds, then an intruder will come in contact with only half of the spies you have and these spies can be thieves or scouts or just auctioneers. [further confusing enemy spying attempts]). It'll also make espionage something that may be backed up with productive work, since Rogue also counts for thievery and stealth assassinating. The spies working outside your guild will then have stable, secure help from within.
I also think it gives a realistic feel to the Outlaws, since that's how outcast societies usually work (take Robin Hood. They had the people that robbed and people that stayed home cooking, farming, hiding, etc.)
And as we all know, the most successful criminals are the organised ones, and they are the real pain in the ass of our societies, not the guys stealing wallets for drugs.
And they usually have pretty simple structures (Godfather, ringleaders, thugs; two divisions: fronts and crime [espionage is usually bought or included as a task of a criminal].)
I hope you can make use of my opinion! I'd love to see how it goes!
