Hmm, looks like a simple enough implementation if you take advantage of Shopify's line item properties functionality.
I can certainly help you take care of items 1 and 2.
Item #3 is feasible, but turnaround time would be contingent upon whether your shipping costs are quoted live from a 3rd party fulfillment service, or simply based on pre-set shipping prices. The former would result in a somewhat longer turnaround than the latter.
In any case, what would be the best way to reach you to discuss your project in more detail?
Let me know and I'll be happy to spend some time to get a better idea of your needs.
Cheers,
James