Insightful and a fresh angle your_mother. I myself am in a position where I tend to romantizise my years in the saddle which is a long time ago now. It sure was alot of fun but also extremely exhausting. The thing that differs from my point of view is that in Sweden where I come from the diffrences in social status aren't that extreme as in the U.S. for example. There are no junkies or guys not in a position to get another job. Most of the messengers here are still young, well fit and well educated guys who has other opportunities in life that just loves riding a bike or are considering their choices in life while working as a messenger for a while.
I know you are talking about the situation in the U.S. but since this is a forum on the web and for international members also I thought I'd give another angle on the issue.