Great post Jim, and many insightful comments from others. I think that it is everyone’s dream to make their hobby into a job; after all, we start hobbies because we enjoy them, unlike many jobs which we do simply to pay the bills.
I think it would take a very unique and special set of circumstances to be a self-employed woodworker. Either you could live in a city with a large population of wealthy clients and you are able to produce unique/fashionable/sought after furniture, or the right combination of luck/skill and social exposure results in widespread acclaim and business. For every Nakashima, Boggs, Maloof and Krenov I’m sure there were equally talented woodworkers toiling away in obscurity.
Rob, Sault Ste. Marie, Ontario