Single order with two kinds of items - how to ship separate boxes and charge for expedite shipping

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My client's Shopify store offers FREE ship and also provide personalized items. If a custom orders multiple items with ANY personalized item and elects the free shipping, no problem. But when the customer tries to use expedite shipping, my client faces a new problem. The cost. 

So let's assume a custom placed an order with a regular item and a personalized item, if the custom wants to ship it faster they pay the extra; 

1. All regular item(s) will/can ship in 24 hours. 
2. All personalize item(s) requires 2 weeks of work and delivery, so the client will ship it in a separate box in the next 2 weeks.   

If the customer picks free shipping, they have no problem to ship two boxes within 2 weeks for free; but since any expedite shipping will cost extra and the store wants to pass the extra shipping charge (x2) to the customer, they can't figure out how to set this up. Is there any app can take care of these situation? They want to let the customer know upfront the extra charge of course, and once they agree to pay the extra they can send regular item and the personalized item by the expedite method. If anyone has solution please kindly share with me, thanks!! 



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