I can't seem to find any good documentation on working with and troubleshooting payment automation.
Kiln is currently the easiest approach to running your own baker in the Tezos ecosystem. It is early in it's development and iterating quickly. But the focus clearly is to help people bake for themselves; as such there is no real need to automate baker payouts to others.
If you are using Kiln to run your own delegation service you will likely need to find a separate solution for payouts for the foreseeable future. Some example solutions can be found in the answers to Looking for a payout script or software