one customer, multiple recurring orders to different addresses

I’m brand new to Shopify. I’ll be dropshipping to customers who often have multiple addresses they need their orders shipped to. Ideally I’d like to allow them to set up recurring orders for each address. In other words, a customer might have 10 items they’d like each month sent to address A, and 12 items they’d like shipped each month to address B.

Is there a combination of apps that would work for something like this?

If it doesn’t exist already as a feature for some subscription apps you will probably need to roll your own subscription app, some order-editing middleware, or use an automation app like usemechnic to script automated order editing to change the shipping address pre-fulfillment.

You’ll also want to hit the /apps forum and ask about subscription app capabilities.