a person who has some money and good credit and an understanding of business can get their cdl and go straight to running under their own authority. its not uncommon for people with some understanding of business
If you are used to working long hours, you should be fine. I just wanted to make sure you understood what you were getting into. OTR does help on your resume and gives you good experience. It's fun to see the country as well. The money really isn't much better than local tho. I do recommend going through a CDL school or community college. Then you're not stuck somewhere. There is also a government grant worth looking into. Also keep in mind that if you can't find anything local right away, OTR will still be an option.