Best way to start

FloridaJohn, you can get a TWIC and Hazmat. You sound like a person who would do very well as an O/O but you need to be in this business as a company driver for at least a year before going in that direction. Learn all you can about this business before investing any money.
The rates in this business fluctuate and owning your own rig means keeping the wheels rolling which means, working local...many hours on the job and as an OTR Driver...many days or weeks away from home.
Trucking is a job with a completely different life style than what you're accustomed to. Most who switch careers and try this...fail. It's hard work, long hours, little sleep and dangerous. Depending on what type of freight you want to haul, it can be physically demanding as well.
Asking questions on this web site is a good start but if you're serious about getting into this profession, visit a few truck stops and talk to other O/O's and company drivers. Don't be afraid to ask questions, most drivers will be more than willing to answer any questions and help you out.
Good luck.