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thousands of products ranging from super tiny and light items to really large items
I do know that such a formula would have to not work solely by volume because as we all know from playing tetris, different things fit better it certain places facing certain directions which allow you to get "full rows" (TETRIS!).
The .50c first class mail envelope, do they do any type of delivery confirmation with that? I believe that would be a requirement for shipping purchased goods.
If the total weight of all the items to be shipped is less than maximum weight allowed for the shipment box, and the total volume of all the items in the order is less than the maximum volume allowed for the shipment box, AND none of the items in the order's length is greater than the boxes L/W OR H, AND none of the items in the orders width is greater than the boxes L/W OR H, AND none of the items in the orders height is greater than the boxes L/W OR H.