Shipping Problem

For background, even though I realize that shipping support itself needs to come from the shipping plugins — please read this all the way to the end: I’ve tried numerous shippers, plugins and configurations, and I think I’ve narrowed down my issue with accurate shipping to one issue – I really need the ability to tell my shipping provider how many boxes my SINGLE item packs into. I deal with numerous small items (printed material) and have bundled into sets so people can order “150” “250” etc – it’s not practical (or accurate) to attempt to weigh a single sheet of paper and have someone buy 150 of them. However, when I get into very large quantities, my shipping company can’t return an accurate quote because I get bumped into freight. Without the ability to tell the API that yes, this weighs 200 lbs, but it’s 5 boxes that weigh 40 pounds each, not a single box that weighs 200 — I’m getting extremely high quotes back from FedEx (right now, though we’ve tried UPS with the same result), because it bumps us into freight when it’s possible that the order could be shipped ground in multiple boxes.

So my question is this – is this something I should try to address with my shipping plugin developer, or is there an assumption at the core of WooCommerce that each single item will ALWAYS fit into one box that he won’t be able to get around? I know that with plugins that allow box packing, it can put more than one smaller item into a box. I need a way to say that a single item will require multiple boxes. This has been going on a year of trying different resolutions, so if anyone has suggestions, I would love to hear them.

https://www.ads-software.com/plugins/woocommerce/