The Cutie Map sends Applejack and Fluttershy to Las Pegasus, where they once again run into the Flim Flam brothers.

Okay, first off? I find the upcoming episode's title and synopsis criminally bad. But then, I've also always had a very specific impression of what Los Pegasus is—an impression, mind you, that's backed up by the official map.

As luck would have it, though, this is already Manehattanverse canon: Los Pegasus is a cloud city, save for the Applewood district, the growing capital of the nascent Equestrian film industry. There is no Las Pegasus, the only ponies who call it that are wannabe Canterlotites with no real knowledge of the world around them, and it's certainly not a city famous for gambling. Orange Sherbet has actually been there, it's part of her backstory, thus it will not change as a result of this episode.

With all that said; does anyone have a headcanon to drop about this situation?

Not much beyond what you just said. However, I would say some of the less informed ponies confuse the pronouncing of LOS Pegasus (actually the Manhattanverse counterpart to Los ANGELES). The actual gambling capital of Equestria (at least in the Manhattanverse) is Las HAYGUS. Unfortunately, some ponies are just dumb enough to get the two cities confused.

My Headcannon (which pertains to your spoiler warning): Flim and Flam are unrepentant, remorseless, pure evil scumbags, who sold their souls for the Mechanical skills that go into their inventions so they could get rich off of them, and redemption is impossible.

5486062

5486910 Nah, the devil offered them $1.95 for both and they agreed.