1. It's all about mindset and how you feel. I am doing 99% better than all of my peers, but I don't feel like it. The very few people who have some insight into my financial health think I am "rich", and I think I am poor. I put away almost 50% of my income - steadily - and I am not even happy with that. It's stressful for me. I don't care how well I am doing compared to my peers, I care how well I am doing according to my own principles. Right now, I am suffering. You need to find your balance and what you feel comfortable with. 50% is not enough for me, but it can be WAY too much for some people.
2. I struggle with this one all the time. I am younger than you and people are always telling me (even on this forum) I need more balance, or I need to spend more money. And maybe that's true... but I genuinely feel worse when I spend money. I rather not buy something, just because I know it will affect my finances. Is that OCD or what?!
But I do know how to have fun - and when I do, I make sure money is not a concern.
I think of it sort of like going out to dinner, but having water and no dessert. What's the point?
I rather blow $60 on a good dinner and have it once a month as opposed to spending $20 on a "restricted" dinner 3 times a month.
It kills me when my mom will go out for dinner and order a water... absolutely kills me.