In your example, if someone were to buy 2 cutting boards but need to have them shipped to 2 separate addresses, then they would need to place 2 separate orders. This is pretty standard across all online stores. Even Amazon works that way – it won’t let you split an order into two separate addresses … it’ll make you place 2 separate orders.
In order to handle the custom engravings, you would just need a “Custom Product Options” app (https://apps.shopify.com/search?q=custom%20product%20options) – there are many to pick from.
Just to clarify, if a customer wanted to purchase 2 cutting boards, with 2 separate engravings, but have them both be shipped to the same address – then they would only have to do 1 order (not 2 orders). It’s only if they need the products shipped to separate addresses, where they would need to make separate orders.