Shipping cost by individual item, dependent on location
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I have ~100 items I ship that due to size I ship individually, and unfortunately, that means that if someone orders more than one item per transaction, it messes up the shipping costs I've set in the Shipping Calculations settings.
For example, it costs me more to ship three 6 lb. items than to ship one 18 lb. item, but the shipping calculator lumps them all together. So if I create a shipping method where 6 lbs = $16 and 18 lbs = $19, I want a transaction with three 6 lb. items to cost $48 shipping.
I know I could set the shipping cost per item and achieve that, but my problem is that I ship internationally and really need the cost to depend on location too, which as far as I know is only possible with Shipping Calculations.
Is there a solution here?
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Sounds to me like you need to move away from PayPal built in shipping calculators and calculate shipping on your own site. You can calculate the shipping based on any variables you need directly on your site, and then you can include the shipping amount in your payment request to PayPal.
The steps for getting this done would vary greatly depending on how your site is currently setup. Are you using WordPress, by chance?
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