You are absolutely right in all that you say. I really have trouble conceiving why someone would be pissed off about the fact that I came to a reasoned decision about what's best for the everyone. Even in my most extreme liberal days, I would have always welcome hearing someone with another perspective, and I would never have allowed said perspective to influence my personal relationship with a family member.
Well then, you were a rare liberal indeed - most likely a product of your upbringing, environment and political culture. Young indoctrinated libs with this attitude, which usually comes with common sense as well (a rare commodity these days), are pretty much destined to jump the plantation fence at some point later in their lives once they realize how things really work in the world.
Another plus is that you're obviously quite intelligent, based upon reading your missive - which I did read (obviously unlike some who have responded to this thread). Ignoring the past support for Obama, I found myself in agreement with the majority of what you wrote beyond that point, although not all. As for the responders claiming the letter was too long - that's probably true. But I can sympathize, since I often do the same thing myself. I'm famous for horribly long emails.
As to one of your original questions about whether this sort of approach would work to sway traditionally D demographics, I have no idea. To me it mostly sounded like logical arguments for conservative ideals, with a bit less pandering (for obvious personal reasons). I'd certainly like to think that's the right approach, since pandering and promising free stuff is absolutely the wrong answer if you truly believe in individual freedom, limited government and free economies. Maybe it really is just a question of getting the message out in minority communities, but I really don't know how you do that. The stupid party (Republicans) hasn't had a candidate since Reagan who bothered to even TALK about and explain, in well understood terms, the pros and cons of economic conservatism. During the debates I heard an inkling of it from Ryan when he was trying to get a word in edgewise with the mean, obnoxious drunk he was sentenced to "debate," but that was about it.
BTW, I had no idea that Obama's claimed position on education is as you state it. I'll take you at your word there, but I find it really hard to believe - meaning he's lying yet again, as he pretty much always does. What has Obama actually done in terms of charter schools & teacher accountability? Answer: Nothing. And don't hold your breath. That's straight up anti-NEA, and unions are the bread and butter that keep that tyrant and his tyrannical party in power - which is all they care about. He will never bite the hand that feeds him and put him in power as a Manchurian candidate, no matter what supposed positions he claims to support on education.