IMHO the stress of being employed is far greater, particularly in these scary times. How many company web designers are in pensioned positions that are secure? How many of their jobs are guaranteed for more than a few months down the line.
Believe me, having your fate in your own hands (once established) is far less stressful.
AFAIK none of the people in this thread have suggested that the $300 site is a good business model. It's just a potential source of additional income.