Cheers!
I've seen quite a few attempts at automatically generating mappings from one data model to another. In the age of tf-idf this was inevitably a disappointment. With something like sbert.net we can certainly do better.
I'd consider two scenarios: (i) migrating data from a production system to an analytics system, and (ii) migrating data from one production system to another.
Let's imagine the system is a hotel reservation system. In the case of (ii) any scrambling of the data could produce a very unhappy customer. You might test the migration multiple times but at some point you have to cut over the old system to the new system and live with the migration you did. In the case of (i) an error might throw off your analytics, but the analytics might help you find errors, and you can always feed back what you learn into the migration process and do it again. (In fact you'll probably 'migrate' again and again to make monthly, weekly reports.)