Alright, after splashing some cold water on my face, I got chilled out. And then started to analyze on what happened, and a few things I figured out.
1. Trying to buy the same item in the shop (not market) won't work. It won't let you spend extra cash on an item you already own.. Example: (You have a Pitch fork, you try to buy another pitch fork, it won't let you and you won't lose your money)
2. However, in the market, that restriction doesn't save you from losing your money when you try to buy the item. Example: You have a Masterwork Longsword in your inventory, you see another Masterwork Longsword in the market for a good price and are thinking of buying it to then trade it for another Masterwork item, you click accept... and... poof! You're money is gone and you don't recieve what you paid for!
3. The way I tested this is I tried to buy 2 leather gloves in the shop (not market) and didn't lose my money AND didn't recieve the item, however, when I bought a Straw Hat from the Market ( not the shop) I DID lose my money and DIDN'T recieve the item.
4. There you go, a bug in a box with a wrapping gift on top. (Hope I somehow get the sword I paid for).