Interesting shipping logic - FedEx + multiple recipients

I have a client with a very peculiar need and I was wondering if this logic is possible at all.
My client sells gift baskets to corporate accounts and individuals as well.

What they need is a way for the user to purchase multiples of the same product and ship them to several different recipients within the same transaction while still executing one single payment.
The other wrinkle is that they use FedEx to ship their perishable products so the shipping charges, calculated via the FedEx API, would be different for each item.

The ideal logic should work something like this:

Purchase 10 items and then enter 10 different addresses to ship it to.
Add a Note for each item (gift card)
Calculate FedEx charges for each shipment
Pay one single invoice through Paypal or credit card

The main issue here is that FedEx charges will likely be different for each recipient and the FedEx module would have to calculate all of them at the same time.

The point here is to make it easy to the corporate buyer to purchase and send multiple items of the same kind.

The problems we had in a previous incarnation of the cart was that users would find a million ways to screw it up. Most notably, some of them would hit the back button at the "thank you" page after they came back from Paypal and in the process erase the order from the database. They did that to get back to purchasing another item for another recipient ignoring the very big button I placed there to send them back to the shopping cart to purchase another item for another recipient.

I realize that Zen Cart may not be able to follow this logic, but I thought that maybe someone else has had this problem and found a good solution for it.

Thank you for your help.

Other problems were that they would forget to fill in fields or

this will NOT work,
you would need to just get an average shipping price,
and add it as flat

Merlinpa1969:

this will NOT work,
you would need to just get an average shipping price,
and add it as flat

Yes, I understand that. I went down the average shipping rate, but on this product this can make a $20 swing in price and it's simply not an option. At least so the client tells me.

The reason I posted here is because I am hoping that the cumulative brain power of the community may help me figure out an alternate logic or an elegant way to implement it.

If I have a customer calculate shipping and then go back to purchase another item and calculate shipping on that it would still be feasible. What I want to avoid is have the customer check out each time and having to return to the top.

If it's not possible it ain't, but I have been surprised before.

Thank you for the input. :D

No because shipping is calculated at check out based on the single cart criteria