What's this? The time shenanigans are getting to a point where my brain is nearly melted from trying to process it all... gah!
Fact: The pages in which
Die goes to the universe in which Spades Slick is dead is noted as "a desert amidst the ruins of a dead civilization."
Fact: Scurrilous Straggler is wearing tattered robes that are like a sun-bleached version of Jack Noir's Jester Uniform, complete with the same logo.
My gut says that "the ruins of a dead civilization" refers to the Dark Kingdom.
Jack Noir became/becomes
Scurrilous Straggler after the fall of the Dark Kingdom, presumably at the hands of the Homestuck Kids. Subsequently, he assumes the identity of "Spades Slick", creates the Midnight Crew (in the image of something brought to them by the Homestuck Kids?), and makes "this town" ...however exactly that happens.
Also, the scar on the eye of the Emperor is obviously due to the Kernelsprite's prototyping by the maimed harlequin. Remember, a "Dark" sprite descended below, while a "Light" sprite ascended above. Methinks there will be "Light Kingdom" counterparts to the Archagents, as well as the Emperor. There may even be "Light Kingdom" counterparts to the Midnight Crew, which for the sake of wild speculation, are the main characters of Problem Sleuth, (perhaps -1)
On that speculative note: though noted as female, Peregrin Mendicant, DOES remind me of Pickle Inspector.
EDIT:
If you weren't so preoccupied, Clover could tell you that you could use Crowbar's help to pry anything out of a time loop, stable or otherwise.
DOUBLE EDIT:
Even further out there, what if he literally "Made" the town, using something similar to SBURB? What if the whole thing is older than anything?