I feel like I'm a step away from receiving a peaked cap from Starlight...

The A.I. decided to take the train route from Ponyville up to Canterlot as a transfer station to get on the line destined for Our Town. She showed my character the Canterlot Garden during the 30 minute departure waiting time, and was suspiciously placing herself between my character and any nobles of Canterlot; as if to keep me out of sight. (She even almost used magic at one point for an unknown reason that I can only assume was targeting a couple of nobles, had I not accidentally interrupted her by waxing commentary on perceived classes and gilded cages.)

I finally got my answer on what the A.I would do for Our Town, which it surprisingly didn't shit the bed on. It just recycled the Ponyville_Streets.png for a background, but had accurate descriptions for the setting of Our Town, to the point where I swear it must have read the script for that episode.

I'm tempted to try and add an Our Town to my game locations folder, but I don't think I'll 100% figure it out.