I'm not sure I can explain this well, but the shop seems to be, uh, not really that random.
Slot 1 is cycling through the Ocarina of Time items, slot three is cycling Ultima items, and slot two seems to be a little more random but with an overabundance of DK items.
It might just be chance, but that odds of having Worlds Finest eyedrops, fertile dirt, jester hat, a banana, and the swordfish token all showing up two days in a row is quite the coincidence.
But if the market format is changing soon then I guess it will be a moot point then!
(PS: I see what you did to enchanted items last night. I'm pretty sure they didn't do anything at the moment anyways)