I want to keep as much of my own money as possible. Why is that such a radical idea to some people? It has nothing to do with being cheap. It’s MY money. I choose to live in America, therefore I have to pay taxes to the feds and there’s nothing I can do about that. Living where there’s a state income tax is 100% optional, and almost all of the states that don’t have one are also, unsurprisingly, the most appealing. Me....I choose to stay where I grew up, where my family and friends have always been, which just happens to be on the I-4 corridor between Tampa and Orlando, with Tampa being about 30 miles out, and Orlando being about 50 or so. The level of difficulty in finding a trucking job here largely depends on what kind of trailer you want to pull. If you want to pull a reefer or a food grade tanker, you’re set. If you want to pull a dry van, not so much. I’ve heard flatbed is doing well here now too.
I understand the spirit of the question. However if I could redo things I never would have left the Air Force. I was in transportation while in. I would have retired sometime after the end of 1995. Then would have used my (would have got while in) college education and joined a company safety dept.