Is this possible?

I have a very intricate set of products and discount rules I need to set-up for our scuba diving shop here in Mexico. To keep things simple I will use regular items, rather than dives to discuss the discount structure.

Our products are:

• Apple^*: $40
• Banana^*: $60
• Orange^: $80
• Pineapple: $80

As a product add-on, these products can come wrapped for an extra fee:

• Wrapping: $10

Discounts required

• Items with a * are eligible for a multiple purchase discount of 10% when a person buys 3 or more items marked with a ^. In this example you can see that an Orange counts as one of the three required items, but the orange itself is not directly discounted, but if an apple or banana were also purchased then these would get the discount.
• If a customer asks for items to be wrapped, this wrapping fee should only apply to their first three items, after which the wrapping should be free for the customer. This free wrapping after paying for three wrappings applies to all products.

Complications…
Where this gets really difficult is that many of our customers will buy items on behalf of friends and family members, but these discounts are strictly per-person. So John might buy the following items (all of which with wrapping):

• >Apple (John)
• >Apple (John)
• >Apple (Amy)
• Apple (Carolina)
• >Banana (John)
• >Banana (Amy)
• Orange (John) — Free wrapping
• Orange (Amy)
• Orange (Carolina)

In the above list, the items starting with a “>” would get a 10% discount:
John has 4 items – He got free wrapping on his 4th item
Amy has 3 items – She got discounts on the Apple and Banana, but not the Orange because oranges count as items but do not get a discount.
Carolina has only 2 items, so she does not get any discounts.

Possible?
Sorry for the long question. So, do you think this would be possible with this plugin?

I am still at the early stages of development, so I don’t have a specific way in mind for the items to be assigned to particular people, so I can be flexible with the configuration of how items are added to the cart.

Any suggestions on how I might be able to achieve this would be greatly appreciated.

Thanks