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This is great progress, really sharp observations about causality. Overall, your plan seems to be on track. If there was only one thing I could recommend, it would be to focus your energies on impermanence, maybe even doing daily impermanence exercises to see what happened as expected and what didn’t happen as expected. For example:

Expectation: The train will arrive on schedule

Reality: It arrived on schedule

Expectation: If the train is on time, I will get to my appointment on time

Reality: The train was on time, but I was late to my appointment

Expectation: If I am late, I will feel uncomfortable

Reality: I did feel uncomfortable

Expectation: If I am late, I will feel uncomfortable

Reality: I was late, but not asuncomfortable as I thought, because others were late as well.

The reason for this daily impermanence exercise is that it forces you to compile instances of impermanence in a clear and detailed manner.  It helps to see all the little permanent thoughts we hold onto in addition to the bigger ones (that you have already identified as problematic).  Right now, you might have a lot of Alana-impermanence examples, but you need to see how pervasive impermanence is in the world in general. A personal/limited view of impermanence may not enough to break through. Ultimately, these daily observations will end up power boosting your weaker contemplations…the ones that you understand but still seem to linger.

People say, “That was then, this is now. There’s nothing that can be done. Just accept it and move on.” Easy to say, but so so so difficult to accomplish. You can’t force acceptance! So what can you do?

The past that has completely changed is now anatta… it no longer exists in the form you once knew it to exist in. But why does your heart still reject this change? Why do you still want the past to be true? Why do you reject the present? You cannot contemplate if you look at it from the “now” – you have to reach back into time and make the impermanent permanent, in order to contemplate its impermanence. While you know it has already changed, you have to go back to “before change” and think about how the three common characteristics apply to it.

You mentioned trying to understand the rules that govern the world. What are they? The three common characteristics. Namely, everything in this world, tangible and intangible, shares the three common characteristics of impermanence (anicca), suffering (dukkha),  and cessation of existence in a conventional form (anatta). Our job is to recognize how they apply to every situation.

Anicca covers arise-cease, it covers the fact that all things must end/die, that change is normal, change is natural. To see this truth more clearly, you need to rack up more examples of impermanence to see how impermanence governs everything.

Dukkha covers that stick in the river. Anything that resists the law of change is called “suffering.” Suffering comes with a timeline: immediate suffering, the harmful consequences that will follow, and dangerous perils off in the horizon. Your contemplations need to span the entire timeline in order to be comprehensive.

Anatta covers the fact that change can reach the end, that you cannot exert control to revert back to what once was, that we cannot control or own anything in this world. Anatta doesn’t need to be contemplated, it is a result of impermanence.

The reason that you see rapes or bombings and still feel exempt or special is because your mind doesn’t have enough evidence to see that you have been in that position, that you can definitely be in that position, and that you will be in that position. It isn’t enough to recognize the factors and causes behind the situation in the news, but you really need to feel the emotion of the situation. It is like when you become the character you are reading about in a novel – you feel the pain, the delight, the conflicts, etc. This is a key skill LP Thoon emphasized as necessary for dhamma practice.

If you contemplate on impermanence enough, there will be no doubt left in your mind that you are definitely subject to those dreadful circumstances. You have to force yourself to see how it has happened or will happen to you.

When it comes to the four quadrants in the matrix, don’t neglect quadrants just because they are similar. For instance, if your matrix is

Skilled/Unskilled leading to Rich/Poor, you have four topics for which you need to compile good examples.

If you are skilled, then you’ll be rich

If you are skilled, then you’ll be poor

If you are unskilled, then you’ll be rich

If you are unskilled, then you’ll be poor

A key point that is often missed is how “skilled” doesn’t necessarily mean “not unskilled” and how “unskilled” doesn’t necessarily mean “not skilled.” Similarly, “skilled means rich” is not the same as “unskilled means poor,” just as “skilled means poor” is not the same as “unskilled means rich.” They are separate topics that all need to be addressed. If you miss any of the four quadrants in the matrix, your contemplations will be left hanging, you won’t be able to draw a conclusion and close the file.

Dhamma contemplations go through phases similar to a science experiment. And after all the testing and observation, you need to conclude in order to make sense of the work and move on. In the conclusion, we go back to the original permanent thought, review information that proves/disproves it, hit on the main why and how, form the new viewpoint, and propose an action plan. In dhamma contemplation conclusions, we often have to incorporate suffering, harmful consequences, and future perils in order to hammer the fear into our hearts. Otherwise, we won’t stop doing what we’ve been doing that causes us pain.

That’s pretty much it. You’re on the right track, just need more impermanence.