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Set different flat rate shipping for different items

I've made items to sale and different items need different flat rate shipping.
As an example, one item needs Small flat rate box. Another needs a medium flat rate box. Both together require one medium box.

Items only have the choice of fulfillment method as shipping, they don't let you specify anything else relating to it.

I've created a shipping region  (USA) and added "per order" flat rate options of small, medium, and large.

I can't find anything that would allow me to pick which items require which shipping rate.

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I made a temporary solution:

 

Set rules for flat rate shipping by weight

0-14.99lbs = $8

14-59.99lbs = $16

60lbs+ for $22


Then go through setting items weight based on what catagory you want them in

$7 flat rate = 1 lb (up to 14 items)

$16 flat rate = 15lbs (up to 4 items)

60lbs+ = $22 flat rate

 

The 60lbs mark: items that are large and fit in the $16 rate just jump up $22 after enough of them are ordered.

And of course if you add items that are heavier, just add a new rate with a set weight, and anything that does manage to reach that weight you know would require a larger box anyways.

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This way

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