SkyHigh - I can say from experience that having a schedule like your friends may feel like the best thing in the world EXCEPT for the certain times of year when the funds get tight and the work is slow or there is no work at all. If it weren't for my furlough I most likely wouldn't have met and married my wife, we wouldn't have had our daughter and I wouldn't have been there to see her first steps and the such. Most likely I would have married a flight attendant - got divorced and be living on have of what the majors are making now after 50% pay cuts.
As you said your friend is living "meagerly" and that is ok for some people. For myself I'd like to be able to buy a bigger home for a second child, have health insurance and be able to have one parent stay at home and raise our children.
One other thought as for doing a variety of jobs is the security. I'm trying to get out of my Baja Bush flying now because of the danger factor. We all know that flying at FL 240 in a state of the art aircraft is a much better place than being down just over the tree tops or flying over snow using a hand held GPS.
BTW - for any charter guys w/ no insurance you can get $500k term for under $20/mo. My wife wouldn't let me fly SEL into Baja without it. Seems like a good deal.
Just my two cents.....