There are trucking companies that will train you, and pay for your CDL licensing, they'll even give you just enough to live off of while you are training. You just have to work for them for a year, and it's totally free. That's what I did. I was lucky too, I lived local to the trucking company, so I was home every single night. Long ass day, but I was home and slept in my own bed. Problem is, the trainer I got was a **** up. And the guy who was my boss and controlled the routing was best friends with this guy. Yeah, luckily I'm a smart enough guy that I was able to muscle my way through it, but I'm telling you, go this route and you are STUCK with the guy who trains you, and you're pretty much his bitch.
So, you have more leverage if you come up with your own CDL, but if you don't feel like paying 4-5k, there are alternatives. If you want some, I'll list some companies that will train you.
2016: **** Your Feelings