I have been on both ends of this spectrum, and when you have more to tend to spend a bit more and when you don't have much you tend to watch over every penny painfully. I have enjoyed both, strict budgeting and spending freely. However, I have never spent beyond my means. I have never borrowed expect for a couple of housing loans which were well planned. Spending wisely is the key, don't go overboard on anything.
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You definitely have it all planned out and figured out as well. It's important that we truly know our financial status because that knowledge alone helps us alone in a lot of decisions we make.
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Nah, it's just the lessons you learn from life.