Will employment history keep me from entering the trucking industry??

Which city are you near?
Lambert Transportation in Denver/Arvada sometimes hires new cdl grads for pneumatic dry bulk tankers.

 

You'd make a good OTR driver. Will you attend a private cdl school or a trucking company school?

 

Either way, private school or trucking company school is ok.
Since you plan to do OTR and stay in the truck, taking time off in different places across the USA, I'd go with a company that has APU's or EPU's and set up for driver comfort. It can be hard to deal with if you don't have an APU and have to take a 10 hr. or longer break somewhere that doesn't allow you to idle the truck.
Navajo Express in Denver is ok to get the career started after attending private school. Nice new Kenworths.
Stevens Transport hires in your area and pays for cdl school and has fully equipped trucks for driver comfort and long haul trucking. I think Stevens also has flat screen TV and refrigerator installed at the factory.

 

If hometime really isn't a concern and you're kicking around the possibility of a CDL school on your own dime, an LTL company might be right up your alley. Estes has a large terminal in Denver, you could run extra board for them and they'd put you up in hotels or bunkhouses all week. Seems the bunkhouses are slowly slipping by the wayside, and some of em (Nashville) are just as clean and have the amenities of a hotel. Knock out doubles, hazmat and tanker while you're in school and off you go. I didn't have good experience at Estes but I was a city driver, and you can't urinate without being told you're doing it wrong. Linehaul they'll flip you bills and you won't hear a word from anyone. And it's Driver discretion as far as running in inclement weather. Which may be a fantastic thing starting out, so some yahoo isn't telling you to find a way around I-80 when it's blizzarded in. Plus, as touched on before, if you tell central Dispatch you don't care when or where you get home, they'll get their weenies wrapped up around their phone cords. You're a dispatchers dream.

 

They have a reputation for excellent training. Do the 12 months there and then there's a hundred companies that will hire you. That's your call though. Plenty of other choices.