Yes, now that I think of it, I have never gotten two items in the same game day, other than Jack O'Lanterns. However, I found that you may have to spend up to 3 stacks to get your first item.
The items I recieved, in order are:
Items for Kerikun (My mule)
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Trick Staff (Traded 1 stack to get item)
Items for Luminara
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Trick Staff (Traded 3.5 stacks to get item)
Pumpkin Head II (Traded 3 more stacks to get item)
Jack O'Lantern (Traded 2 more stacks to get item)
Jack O'Lantern (Traded 3 more items to get item)
Horror Hat II (Traded 2 more stacks to get item)
Jack O'Lantern (Traded 2 more stacks to get item)
Trick Staff II (Traded 1 more stack to get item)
As for my method, I would use only oranges and go around to all of the NPC's in a circle, then go to Northern San, circle NPC's, return to Southern San, and so forth.
Boiling this down, it does seem valid to me that you don't get more than one equippable item per game day.
EDIT: Fixed seperation of item list between characters.
Edited, Mon Oct 25 05:51:53 2004 by Doktaru