On 5): The most transformative step in my journey up the class ladder was when money stopped being a source of problems and instead became a way to solve problems.
I have plenty of money (relatively speaking, I don't make FAANG money but I don't worry about paying the rent or saving for a rainy day). I have real trouble spending it though. It almost causes me physical pain to spend money on something I don't regard as essential. I don't like to travel, or eat expensive meals, or go to movies, concerts, shows, etc because I hate to spend the money on it. Don't know what the root…
I save money by not buying much stuff in general. So when I do have to spend it’s not a big deal. It’s not like saving $80 by not going to a concert would have some profound impact on my future financial situation. Same with vacations or buying clothes. I don’t do that stuff often, so when I do, whatever. Why ruminate so much on it.
I used to be more of your mindset but realized it was stupid. And you end up missing out on opportunities if you’re too frugal just for the sake of it (rather than necessity). People I’ve met on trips, random books I’ve bought, etc have changed my life in lots of positive ways.