Wonder why the interest on the student loan was so high. I consolidated mine around a decade ago at 2.5%. Does the generally low interest rates over the last few years not apply to student loans?
Other things to add. The key here is to understand pre-tax cost vs post-tax cost. For example, that $500/month you save by not hiring a maid, a gardener, a pool guy, and being off cable is post tax saving. Depending on your tax bracket, that amount may have been $700-900 pre-tax. Looking at things from that prospective really magnifies the importance of saving and keeping your monthly overhead down.