I've got an inquisitor who infiltrated the lower levels of the Last Laugh. I've actually written up the Last Laugh and Alleybashers as 2 competing organized crime families similar to the Godfather movies, with Ankhin Taskerhill as the head of the Last Laugh and Zachary Aslaxin I as head of the Alleybashers. Just like in the movie, neither family head will ever give direct orders to commit crimes. They do it through a series of underlings so that they can never be fingered short of high power divination spells. Inbox me for my simple wiring diagram for each family and associated businesses each family owns or interacts with.
Our inquisitor began by helping one of Fish Weijeron's (Caporegime of the Wererat Regime) low level button men (also an employee of Arlintal Shipping Company's Cauldron warehouses) steal some high dollar wine and sell it on the black market. The inquisitor did this enough that he gained a small amount of trust and was brought in for an interview for a full time job within the regime (most button men in my campaign are hired on a job-by-job basis). They blindfolded him, cast silence on him, darkness, etc and then drove around until he lost his bearings) and brought him to Fish for an interview. Fish was wearing a hat of disguise and looked like a halfling so that he couldn’t be recognized later. Of course while the inquisitor was there, the LL scanned him for alignment, detect thoughts etc and learned that he was good-aligned and wasn't wholly telling the truth about why he wanted to work for the organization. They opted not to make him a full time employee but offered him a part time job smuggling khat (a illegal mild narcotic) into the city. He gets 200 gp per month (per chapter for ease of accounting) for the work. We have since ceased role play on this thread and just let the story work on autopilot in the background of the campaign. Little does the inquisitor know that the Last Laugh now has pictures of him smuggling khat, stealing from Arlintal, etc and plan to publish a story in the newspaper if he or the party ever accuse the LL or related public figures of corruption etc That should be coming out in another week or two.
I also have an email string associated with this role play for anyone who is interested.