you can offset the "loss" of your initial donation like nothing and start profiting from it immediately, even on a single transaction with just a handful of items.
Why is that a bad thing? Loot less, play more!
Because it's gimmicky.
Sure, it's convenient for the player, but not everything that's convenient is better for the game.
In this case this "trick" actively encourages the leverage of a cheap exploit for profit, while also making the other alternate trading system currently included as a "viable option" in the game intrinsically worse in comparison.
And while I usually try to not appeal to "realism" when we are talking mechanics, a degree of verisimilitude remains relevant.
So it's hard to ignore how the current system makes no damn sense in general. No merchant would ever give you discounts piling up in the THOUSANDS because even if you were complete strangers minutes before, you introduced yourself giving a wink and putting a fifty dollars bill in their hand.