Custom selections and input from customers during subscription / custom subscription frequency

[MagiMoBoxes]

Hi all! we are stumbling with a few scenarios that we desperately need help with!

First scenario:

We have a subscription based business that is holiday based. Therefore, some of the recurring shipments/orders have "options" for the customer such as chanukkah or christmas. Is there a way to ask customers to confirm a selection before the recurring order is shipped?

Second scenario: 

We want customers to be able to buy a "gift" membership (for example, 3 boxes). In that case, we will either want the purchaser to select the three boxes for the recipient (example: easter, 4th of july, halloween) or have the recipient have the ability to select. In which case, we will also need to be able to send the selection options to the recipient for them to select. 

Bonus scenario we need help with:

We need suggestions of how to manage the subscriptions that do not have fixed intervals for charge/shipments. For example, our valentines box needs to charge/ship Jan 21 but our 4th of July box needs to charge/ship June 7. 

Please HELP!!!!!! Beyond appreciative for the assistance. 

Thank you!