[aixguy]

Mark, I can't really answer the first question but I can comment on where I was in 1995. I had been working as a full time automechanic for over 10+ years of my life, recently mairred with a firstime small (old) home that we could just about afford. No kids, so you have much more responsibility than I did. I was sick of the heat/cold/wet/dirt and pain of 6 days a week standing on concreet. I was very lucky that an aqaintence of the wife helped me find my way to a new career in computer programming (that was 11 years ago). When I finaly found a job (14 month search) I took a big pay cut, but after a year I was well over what I had been making as an Auto Mechanic.
All that said, you are 33 years old in a young mans business, there is money to be made doing custom painting, whether that money is in your area of the country I can't say. Is it worth it? Finding skills that can produce income without physical activity is very worth while as you get older.
I know this wasn't the answer you were looking for, but we have more than a few people here making a living at this hobby. I am sure they will give you more meaningfull insite into the pros and cons of making a living with an airbrush.