Advice and Perspective

You've been considering trucking for 7 years or so. Are you going to get rolling now?

 

I'm a VET but didn't go through all that. I just wanted quickest way to get a CDL and hit the road.
For me, I just wanted to get moving and not mess around with all the apprenticeship stuff. Truck driving is really a simple task. Some people give lectures about trying to make it as if you're training to fly a space ship to Mars. You've been driving city buses, which is much more complex than trucking; dealing with the public and traffic is too stressful.
The companies I listed are the quickest way to hit the road and start making money and starting a retirement account.
Anyway, the companies I listed are about the best I can do for you. For me, the open road and coast-to-coast & border-to-border trucking is what gives me job satisfaction.
Let us know how the new career is going. Best wishes.

 

From your list, I'd say probably JB Hunt and Roehl.

 

Did you go to Japan when in the Navy?
Japan is recruiting foreign truck drivers. Can buy a house over there super cheap also.

 

Always learn something on TTR. I googled Japan needing truck drivers and there is a shortage there. Never heard of it but not surprised first world countries need drivers. Ironically it sounds like the "shortage" we have here in the USA. According to reddit it's low pay, long hours and you've got to have N4 level Japanese language proficiency. If they did away with the language part they could probably fill those empty seats and keep the rates forever low.

 

JB Hunt has a reputation of paying well. I haven't worked there because it's dry van. My first trucking job was dry van, because I didn't know any better. Dry van is like the bottom of the barrel in my opinion.
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Roehl seems very good. I also haven't worked there. Pay & benefits seem better than average and a mix of dry van, reefers, flatbed, conestoga to choose from or try.
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Personally, I see nothing wrong with trucking company cdl school. Sure there's a contract which varies in length by company.
You get a cdl with a contract to work for X number of months and if you finish the contract the cdl school is free.
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Usually, drivers with a chip on their shoulder are the ones complaining about trucking company cdl schools and sometimes even private cdl schools.
They gripe and say, "You don't need all that; just go to a farmer and haul hay and learn to drive that way. Then go the DMV and get the CDL." Doesn't work that way today. Maybe 30 years ago, but not today.