How to automate

Step 1: Do it manually. Enough time that you get a familiarity with the task. Learn the shape of it, pay attention to the edge cases, look for patterns. Record as much data as possible.

Step 2: Once you've noticed a pattern, build a system to replicate the manual steps.

Step 3: If the system is capable of operating by itself you're done, else go back to step 1 but faster.