My vote is for the "Charlie the Barbarian" option. It just makes the most sense to my mangled mind.
Here's one way it makes sense to me: Charlie, whoever and whatever "he" (for lack of a determinate gender) is, worked for a side a long time ago. Possibly as a caster, possibly as a warlord, possibly as a piker. This side either has or gains the Arkendish. Maybe Charlie has a hand in this, the way Stanley did, but not necessarily. The side is then taken down and taken down hard. Given Charlie's behavior it is could likely be the result of information getting into the wrong hands. Charlie manages to get away with the dish as a barbarian, and is at this point attuned with it. Not having the having the ability to start an official side, he finds a stronghold in the mountains and begins the work of "carrying on". As a barbarian, he cannot manufacture units, but as an arkendish wielder he can produce archons (some of which have the capacity to produce golems), which he then does. Of course, the limitations of technically being a "non-side" go beyond production and he finds he cannot expand, nor can he maintain his forces via traditional methods (such as sacking and pillaging and threatening like a civilized overlord). The only way a barbarian can manage to either be sucked up by a side (unacceptable in Charlie's case) or hire out as mercenaries. The archons and the arkendish both provide an exceptional amount of power and versatility that allow him to function uniquely well as a mercenary unit, but he suffers two additional limitations. First, he discovers that it is a "bubble" business, as others have described it, with ballooning expenses that can only be paid through expanding markets that can only be managed by increased workforce which then requires greater expenses and the only way to keep from collapsing under the weight of it all is to keep it growing. Second, the huge amount of resources and influence he controls would make him a very tempting target if anyone ever figured out he was a barbarian. As a result, he "fakes" a side, calling himself an overlord and setting things up so that his odd behavior is viewed by clients as eccentric rather than desperate. Of course, Charlie has learned the lesson about loose lips and sinking ships, so he controls information as tightly as possible, trying to portray this trait as beneficial in a mercenary company rather than a sign that something isn't right.
That's just one possible theory (I've got a half dozen more that are no less fleshed out), but there are a couple other thoughts I had on Charlie and his archons:
* Charlie is not the dish nor anything more alien than Parson. Charlie is described as being able to share his abilities with archons, particularly his inner circle, which in turn means that not all the work attributed to Charlie is done by him. The autonomy of the archons would allow him to assign one of his inner circle to each theater of war, thus creating a very shallow hierarchy with extremely minimal loss of information control. Never underestimate the power of delegation in the hands of someone who can do it correctly.
* Charlie refers to the Battle for Gobwin Knob as "the great western conflict". This insinuates a few interesting things about his perspective, particularly that he considers it to be limited to possibly 25% to 50% of his potential market. That kind of percentage requires some careful consideration and, until he included Parson into his calculations, he was being very conservative about it all - it was only his greed for Parson's brain and bracer (sweetened by the promise of the pliers) that caused him to make choices that have damaged his credibility. Yes, he was holding out at first for more money, but that only makes sense: if he pushes too hard, he dillutes his value and the prices he can command per archon would drop while their upkeep did not. If you want to make the big bucks, you make sure they know you're worth it and you make sure they know they can't get the same quality elsewhere for cheaper.
* Charlie knows each casualty by name. 600 archons and he refers to each by name when fall. Surely, part of that is due to the arkendish, but I think it also hints at an aspect of his psyche. Most erfworlders don't seem to bother learning about their subordinates, probably because they die so quickly and even erfworlders seem to know the pain of loss. It's a defensive mechanism, since numbers hurt less than names. It's only after you lose just about everything, when all you have left are the few stubborn handful that didn't have sense to leave or die, that such a mindset breaks and one begins to have the same value as one hundred or one hundred thousand. Stanley is a moderate example of this. I think its quite possible that Charlie is even more so. Of course, he could also be using their names as a ploy to justify charging more next time. That's the fun of Charlie. He's kinda like an rorshach test, so ambiguous that what you see says more about you than it does about him.