I left my job in the 90's with less 'life line' then you appear to have. I've owned my own company (in partnership with others) ever since. With the things you've done on the side you appear to be on the ball and ready for it. I was lucky to have partners who compensated for my weaknesses. It sounds like you even have that base sort of covered with the people you know in the industry.
You mention guilt about others not finding jobs in this economy. Think about it this way: If you start your own thing maybe you could end up hiring people into a company that doesn't have a lunch bell (do u guys play dodge ball after lunch on the playground - that would be cool). In other words as a company owner you can shape the world more than you can as an employee (potentially).
If you're a methodical planning type you might want to slow down and do some paper and pencil introspection. I used a book (http://www.amazon.com/gp/product/1883487242?tag=openlibr-20) back in the day (circa 1992) to plan my transition from a day job to a self employed person. This book has questionnaires that are aimed at determining whether you are the type of person that can survive on your own. I flunked them all and went ahead and quit my job anyway (just because I wanted to) but the book did remove my illusions that it would be easy for me to make it on my own.
Anyway - good luck and get yourself happy.
Joe