Thanks for the positive support and info!
As for the insurance, only one company regularly insures hot shot drivers, Progressive. However Progressive Direct is stupid expensive. After much, much, much reasearch and calling I found an agency that specializes in Hot Shot drivers. They still write through Progressive, but get special pricing due to their relationship.
I have a perfect driving record. Insurance alone on the Truck/trailer is about $2,800 a year. With my load coverages and other liability insurances and such my total business insurance is a bit under $5,000 a year. Add in the other $2,000 or so for multiple permits, fees, and other owner/operator government costs, my total yearly nut for paperwork alone is about $7,000. If I moved to a big rig that would near double.