For three, I've been trying an approach that I took from an HN article a while ago. Instead of a Playbook, create a Python script that just prints text for each step and prompts for YES to confirm the step was completed. Then, I automate the most confusing or particular parts. Need a particular user to perform the task? Query for it and make a link to login as that user for the operator of the script. You get a lot of the repeatability of a fully automated script and slowly improve it over time.