Product Shipping Options Question - How do you deal with it

#1
Is there a way for the system to recognize when items are leaving from more than 1 warehouse and update shipping charges accordingly, while combining shipping charges when they leave from the same warehouse?

For most products I am drop shipping offering free e-packet is the best choice as product costs around $20.
I am sourcing from 4-5 different suppliers and this keeps things simple
But

A few high end items can cost up to $200. Therefore I was thinking about adding a DHL/Fedex option just in case customer wants.


Question:

Is there a way to manage shipping costs for items leaving from different vendors, and combining shipping costs when they leave from same vendor? There are woocommerce addons to create "per product" shipping classes. But I can imagine a situation where someone buys 3 products from 2 different vendors, and asks for DHL shipping. If this scenario happens I would not make money, as customer would expect all items to arrive via DHL, but items would be leaving from 2 supplier warehouses.

Is there a way for the system to recognize when items are leaving from more than 1 warehouse and update shipping charges accordingly, while combining shipping charges when they leave from the same warehouse?

Any thoughts/ Question make sense?
Thank you