Automating our processes

Hello,

I began building our platform in Wrike starting back in March and launched 7 weeks ago, so total newbie. I am starting to rely more heavily on automation but I am having difficulty getting them all to function as intended. Some of the more complex goals in automation do not seem to give me the same results each time.

As you can tell from the first pic below, we use a Project to capture the work, budget and overall timeline. Then there is a Main Task (called TASK Test below) which is how we track progress of the work as the Task moves across our Board View. I built the different phases for several reasons; to capture the different components that go into our Task, track our internal costs in the phases and act as a status trigger for Board View.

Problem 1- I cannot seem to automate the Task to move as "All direct subitem statuses change". I suspect that they may not mean this literally because as soon as I add tasks below each phase the automations cease to work. 

Problem 2- I have had a Custom Item automation work on a small isolated series (3 tasks) and then could not reset and replicate this again. Each time it failed to trigger the same action. 

Questions:

1. Do the Custom Items have a memory? 
2. Is it better to build the automation against the custom item and not the location?
3. When they say "All direct subitem statuses change" do they mean every single task inside the project or just the ones below that particular task? ("Phase" in my case)
4. Would it be better to get rid of "TASK Test" and just track each of the Phases on a Board View?
5. Any recommendations here?

Thanks!