First of all, Epic thread! (though it makes my head hurt to read this...)
Secondly, I can relate... Being or trying to be a good mustachian can be a lonely endeavor.
Most all of my friends (now- mostly former friends) where all ridiculous spenders. One of my closest friends once told me (when I asked him if he was saving anything) that his goal was to cash his check on Friday and be broke by Monday. He wanted to enjoy his money and not worry about the future. We went to some steak place and I ordered a reasonable meal. He made a show of ordering the most expensive item on the menu and only ate half of it. When they asked him if he wanted a doggy bag, he scoffed and said that was for poor people and that they could just throw it away...
My family, to some degree, is nearly the same. Spending for the sake of spending. My uncle recently turned 80 and he's still working! Why? Because he's too deep in debt to stop. The same uncle and aunt have 3 new cars (one of them was for their daughter).
It seems like all my efforts to gently nudge these people in a different direction is met with disdain. My sister rarely talks to me- she thinks I lecture too much. I do (not all lecturey, at least I don;t think it's lecturey) but I do it from a place of love. I try to show her how to fix the mess she's made but she lets it go in one ear and out the other. Her method, while not religious, works similarly. I call it the "stand here with my hand out until some one gives me something" method. It actually works!
My sister purchased a car when she was 18. It was a junker. I tried to help her with it. She didn't care. Even "tricked" me into fixing her brakes (an emergency that I had to stop what I was doing to fix)- the pads were gone and the caliper was digging into the rotor (it was supposed to be so she could go to a job interview)- The next day she was off to some amusement park two hours away! When that car died my parents gave her a car along with who knows how much money for an apartment. Her and her husband proceeded to trash the car. She moved. His parents gave them a car. Also trashed. Eventually, she purchased a car on her own - she was proud that she had managed to do it on her own. When I asked if she got a good deal (knowing that I'm a car guy and would have scoured the planet to find her the best deal)- she told me "probably not but, I did it on my own"- I had to bite my tongue. (turned out that she signed a 96 month contract!!! WTF?!?!?) Eventually, she gave the car back to the dealer and my parents gave her another car. When that one broke, they gave her another car... See a pattern??
And I get grief because I'm lecturing...
Luckily, the whole family knows I'm a hard-ass when it comes to money and while they all think we're rich (we're both professionals), no one dares call me to ask for money. I guess there's a good side to it after all.