Wow this is a well documented trip and I love what you have done with the analysis and descriptions and the way you linked each experience and encounter with a moral lesson and I will try my best to chip in my view on each of your moral lessons.
The same goes when we walk our spiritual path. If we leave behind us the disturbing thoughts, the depressing memories, the heart-clenching emotions and make a bold choice to begin fresh and light, everything changes and becomes easier.
Talking about travelling light and how it applies to spirituality. I will be talking in terms of forgiveness. Many people don't know how good it is to forgive anyone who offends us. Forgiveness means dropping the heavy weight you are carrying and having a lighter one to continue with your journey. This was the light I caught from this.
Many people will tell you how to live your life (including yours truly), but the best and only source you should follow is your own heart and soul.
We should learn to live a life of non conformity. We are all unique in our own way but we are always distracted by the things around us that we get so confused and feel following the crowd is the only way out which is not