So, I've been keeping watch on your thread and think that your idea is great, and even though it's on hold now, I am hopeful that you will get back to it at some point in the future. It looks great as an idea, and I think it would be great if you can get everything implemented. Anyway, from following your idea, I had an interesting idea and decided to share and see what you and others thought. Towards the end of the quest line, and if you've joined the stormcloaks and gotten the civil war about halfway done but not finished it, there's an extra quest that shows only under those conditions. The idea of the quest is that Ulfric wants to make his bid for the throne of the High King more legitimate, and after hearing of the slavers guild, gives them a proposition. Bring him the subdued Jarl of Solitude (can't remember her name) so that he can beget an heir through her, and when he becomes High King he will make the guild a legal and reconized guild in skyrim with his backing.
On the other hand if the civil war is going in favor of the imperials, the guild decides to have the Jarl of Solitude captured, broken, and in their graces before having her 'rescued' and returned to Solitude to give them some breathing room with Solitude and the lands under her rule and those loyal to her.
