Yes, you are over thinking it, IMO. Fifteen years ago I graduated with $75,000 in student loan debt, but it put me in a position to earn that and more.
What does a high school diploma get you income-wise? What does a college degree get you? Now certainly with the economic fallout, the answer to those questions have changed a bit but bottom line is college graduates earn more than high school graduates, and have a lower unemployment rate. Where would you be without the degree the loans financed?
I will admit that when I first graduated and got a job, I put myself on a repayment plan to get the paid off in five years. Then life happened (i.e., kids) and I refinanced them for 25 years. Sounds silly at first, but in 20 years the $200 payment will be about the same as filling up the family car with gas.
I never feel burdened by my loan payment. I borrowed against my future earning potential and it paid off. Life isn't always easy but that's life.