> What's something someone with a strong entrepreneurial, technical and managerial background (and very good pedigree) can do for maybe 20 hours a week and still pay the bills? I would love to drop out of the race for a few years and smell the roses.

Consulting. Small business. Almost anything really.

How hard is it to make some $5k per month if you have a skill that you can charge $100+/hour for! About a week and a half of work per month.