Let's say you have 3 identical NWT Canali suits. Which one is more valuable,
the one you bought for full retail, I would expect to lose money on.
the one you thrifted for $10, I would be happy to sell for a few hundred. (this one is more valuable, from a flipping perspective)
or the one Grandma gave you for Christmas? I would not sell until after Grandma had died, as she'd always ask "why don't you ever wear that nice suit I bought you?"
Therefore, I could not approach pricing my 3 identical NWT Canali suits the same way. Might average out to a profit in the end, if all 3 sold, but I'd lose my ass on the one I paid full retail for, would make a tidy profit on the one I thrifted for $10, and would have to wait until Grandma died before listing the 3rd one by which time it might be out of style and I'd make nothing on.