Let me help share information about how you can reorder products with the same name but at different prices.
To start with, adding a new item with the same name as the existing one is not possible because of the naming conditions. This is the reason why you're asked to change its name every time you add it to the system.
That being said, you can still reorder the same item and you don't have to add it to the list again. Instead, manually change or enter the price of the items directly on the transaction when reordering them.