I don't think you're likely to make any breakthroughs with the crowd you've had a difficult time reaching thus far. What can you do differently next time? Try harder? Presumably you're already trying very hard, and you've also tried "trying harder" following each time you've received negative feedback. Write even more painstakingly nuanced sentences? You'll dilute the quality of your writing if you do that. I'd like to see you just ignore the portion of the audience that is consistently not understanding you - focus on getting the message across to at least a minority of people first, and then those people will be able to help you polish your message and deliver it to a broader audience.
I know that the content itself is clear. The main thing that I need to work on is making my writing more engaging to a broader audience. If the writing isn't appealing enough to motivate people to read carefully, I'm not going to get through to them :D. I think that Scott Alexander / Yvain would do a better job than I can. I don't expect to be able to get up to his level, but I hope to move in that direction.
At age 17, my future looked very promising. I had overcome a crippling learning disability, and discovered how to do research level math on my own. I knew that the entire K-12 infrastructure had failed to figure out how to teach the skills that I developed, and so I felt empowered to help others learn how to think about the world mathematically.
Things didn't go as I had been hoping they would. My years between 18 and 28 consisted of a long string of failed attempts to help people learn math, and to promote effective altruism. I learned a lot along the way, but I didn't have the outsized impact that I aspired to. On the contrary, I was only marginally functional, and I alienated most of the people who I tried to help. I found this profoundly demoralizing, and struggled with chronic depression. If I had died at age 28, my life would have been a tragedy.
Fortunately, at age 29, I'm still alive, and after spending a decade wandering in a wilderness, I've gotten my act together, and am back on my feet.
What I finally realized out is that my failures had come from me having very poor communication skills, something that I had been oblivious to until very recently. Recognizing the problem was just the first step. It's still the case that most of what I try to communicate is lost in translation. I know that the issue is not going to go away overnight, or even over the next 6 months. Sometimes it's frustrating, because my self-image is so closely tied with my desire to help people, and even now, in practice, most of my efforts are fruitless.
But I'm not concerned about that. I probably still have 30 or 40 productive years ahead of me. I'm ok with the fact that no matter how hard I try, I fail most of the time. Y-Combinator founder Paul Graham emphasizes the importance of relentless resourcefulness. Every failure is a learning opportunity. I know that if I keep experimenting and learning, eventually I'll succeed. Figuratively speaking, I know that even if I lose dozens of battles over the next four decades, in the end, I'll win the war. And that's enough to keep me going.
Something analogous is true of everyone who has a strong passion, and is willing and able to learn from failure. Steve Jobs expressed a similar view in his 2005 Stanford commencement address (transcript | video):