ray, get a license and ins. and come join us on the contractors forum. It sound like you're ready to make the leap. Contracting in my neighborhood without a license is a felony, doing it without ins. is idiocy in today litigious society.
This is an invite. Come over to http://www.contractortalk.com/forumdisplay.php?f=44
and introduce yourself. Explain that you have a desire to go into the painting business. Then make a similar post here http://www.contractortalk.com/forumdisplay.php?f=8
and you will get the info that you need on becoming legit. I'd much rather see you as a licensed contractor than some jackleg that loses everything that they own due to a single mishap. This CAN and DOES happen multiple times every day. Great bunch of guys and gals there too.