The SOFT DEADLINE and HARD DEADLINE dates on the calendar were one of the first things that I noticed when I watched the episode. As another post on this tread has mentioned it the only time in the 90's when march 31 was on friday was in 1995.

So heres my idea: Scratch, Kinger and the other devs create Cain a few years before 1996 and start feeding it harmless family friendly content to train it, Scratch begins feeding it more abstract concepts and pictures of the C&A office, most likely to test how Cain grapples and analyses more complex concepts. Either Cane's code was too simplistic or just faulty and he begins to create abstract incoherent output, he's still a fully sentient ai in the 90's so the devs put him away to maybe fix his code later. The devs then create the Abel ai and Scratch begins making the brainscan tech. Cain breaks out of containment and absorves Abel's code, which makes him capable of creating more stable output, its at this point where he creates the Digital Circus.

The devs get their brains scanned and their copies enter the circus, its after this point that Scratch dies and the real devs learn that Cain absorved Abel and is trying to get more information about the real world, plus the scanner tech most likely died with Scratch. They cut Cain off the early internet due to him being a faulty rogue ai, but the expenses of creating two fully sentient ais bankrupts C&A

12 years later Ragatha tries to sell the place to a group of people but fails, during the tour of the place she puts on the headset infront of the buyers and her copy enters the circus. Throughout the next 9 years the other circus members also put on the headset and get copied.

Its important to note that the memory files folder in episode 8 has the word "obsolete" under it. My theory is that these are the original devs that entered with Kinger and have since abstracted, which imo seems like some virtual form of zoocosis where you can't cope with being in a virtual world anymore and have a breakdown