Combining shipping multiple addresses extension with product add-ons extension

Hi,
I am struggling to find the best solution for the following:
We sell nice wines with a personal message from the sender for the receiver.
Now many people want to buy wines for multiple addresses and add different personal messages to each wine.

So i was wondering if the following would work seamlessly:
1. Customer adds the personal note to each product which they add to cart afterwards (so with product add ons i can add textfield to each product)
2. Then in check out can add the wines to different shipping addresses. To not get any confusion i am wondering if multiple shipping addresses extension would show this text filled in with the product add-on when placing products in the different addresses.

Or do you have a different idea on how to tackle this all at once.
Thanks up front for any feedback!

Kr Rody

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