Hi there @PR2005.. Thanks for the tag, @Sammie_C.
I'll admit this is not only interesting, but very complicated. I can't imagine that any POS system has been set up for this level of complexity and customization at the item level. Of course, the issues are multiplied by the fact that Xero comes into play.
I can't think of any possible workarounds that don't run into a solid wall at some point. I even tried to figure out if you could use Zapier/Pabbly to possibly automate this, but even then there doesn't seem to be a way to reach your ultimate goal. There are just too many variables and possibilities.
At first, I thought that using payment links was the culprit here. But even if you abandoned those and used the traditional online store with multiple categories and multiple copies of the same items, you'd still have the issue of dynamic pricing that is dependent on drop off location. With a full online store, it is possible that you could handle this with shipping rate customization, but since I'm not a shipper I can't possibly address how or even if that would work.
I'm sorry not to be of more help. Honestly, given the uniqueness of your situation, I'd recommend that you hire a competent software engineer. There certainly has to be a way to do what you are wanting to do, but with the tools available to the general public I can't see a way that doesn't involve some pretty serious software design and coding.
Chip A.
Square Expert & Innovator and member of the Square Champions group. (But NOT a Square employee, just a seller like you)
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