Thanks Adam for the detailed reply.
FunIOUC, you can only lower your own entropy. Thus lowering the entropy of the entire system. You cannot lower anyone else's entropy with your choices. No matter how great an environment you set up for others so that they may also lower their entropy efficiently, it's their choice to do it or not.
I do understand that the most important thing I can do is lower entropy. I guess I sometimes do forget this though. However, my degree is in engineering (Systems Engineering to be specific), so I am always looking to optimize things. If I feel a desire to help people, I want to be as helpful as possible for my effort.
For example, a month or so ago I was seeing all the news articles on the devastation from the hurricane in Texas. I felt sorry for the people, and I wanted to help. Sure enough, many ads began showing up in my browser from well-known charities requesting help. But I wanted to make sure that the maximum benefit would occur from my help. So I did my own research on what percentage of proceeds to various charities actually get to the recipients (vs. paying someone's salary or for advertising). I also felt that a charity close to the location of the disaster would be more effective in wisely spending contributions than one located elsewhere, since they are familiar with the local area and see the specific conditions at the moment. Ultimately, based on my research, I decided to give to a food bank located in southern Texas. Perhaps my contribution did say 30% more good that way than if I had given to a well-known national or international charity. As an engineer, I want to optimize results. Ultimately, I care about the people I am helping, and I definitely don't want to do something that ends up hurting (enabling dysfunctional behavior that ends us raising people's entropy). That is why I have been asking the questions about specific situations - so I can understand how to "calculate" how helpful a given action on my part will be and thus optimize my actions.
The answer to this is to "taste the pudding" as Tom says. Are you having negative emotions? Do you have ego? Do you get upset? Do you get angry? Are you choosing to feel negative emotions? These are signs that your choices are not really lowering your entropy. If you find you are rarely angry if ever, you are helpful to others, are making choices with intent focused on other, and are Love based, then it is likely that your choices are reducing entropy in the long run.
I do try to pay attention to my own intuition. For example, I recently had dinner with a representative of a charity I have supported for many years. He asked me if I would commit to monthly pledges. I replied no, and he asked why. I explained that I try to follow my feelings about what is best, vs. calculating intellectually what I will do ahead of time. I gave him the example of the contribution I had recently made to help hurricane victims, because I felt was what I felt passionate about at the moment, and explained that if had planned contributions in advance I would not have been able to be as flexible in following my intuition and passion.
I also realize that my motivation is important. If I intellectually determine that I should give, but emotionally don't feel like giving and do it grudgingly, I am pretending to be someone I am not. I have taken this into consideration since long before I read MBT. When things are going well for me (which I usually find is when I am able to work at things I enjoy in my paid job, volunteer work, and hobbies), I find I experience a general absence of the negative emotions you mention. At those times, I tend to be a lot more generous with my giving than at times when things are not going well. Maybe it sounds like I'm trying to "bargain" with the system - to say "LCS, you make my life go well and I'll give x amount to charity!". But I don't see it that way. I see it as being authentic, expressing the actual quality of my inner being vs. what I have "calculated" I "should" be doing intellectually. 2016 was a very good year for me. Even though my income was not significantly different from what it was in 2015, I gave almost 3 times as much money away as I did in 2015 when my job and life sucked.
You must shift your mindset towards extreme SELF entropy reduction. Then you can be sure that your choices are reducing system entropy in the long run.
I am an avid reader of self-help and personal growth books. My motivation? If I'm honest, probably because I think that improving myself makes my own life more pleasant. But I'm sure that getting my own life in order also benefits others, not only because I tend to be more "giving" when life is going well for me, but also because having an improved personality can make life more pleasant for others who I am around (at work, with personal friends and relatives, etc.).