A real shopkeeper would not buy back an item he just sold you if it would mean losing money. And he certainly won't do it 100 times in a row. If he wanted to reward you, he would have given you free money.
Merchant:"You are not satisfied with one of my item? Well, todays only, return it back and I will buy it at 150% of the retail price! You can even buy it back again after that and turn it back again!"
Same thing for shopkeeper buying something you just stole from them.
Merchant:"OH! What a coincidence! I have the exact same weapon! I thought it was unique! Of course I'll buy it!
Wow! You have another! I'll take it too!
(6 hours later)
And wow! a 500th one! I want it! too..."
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Once upon a time in Canada...
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