This is a long shaggy dog answer to your question, but for the benefit of others reading this forum I submit it.
The hardest area of trucking to attract drivers is OTR due to the conditions, pay and hours. Competition between carriers drives revenues down and so far, companies are able to fill the seats in spite of conditions and pay. Going to school to get a CDL can be expensive so one of the ways the companies attract candidates is to have their own school, which is usually more expensive than a private school. But they mitgate the cost to the student by hiring them and indenturing them to a minimum period of driving before part or all of the tuition is paid. Often these companies, also known as 'starter' companies will require your working one year or two before the debt is covered. The pay is low...0.22 to 0.30 per mile are common numbers. Even at 0.30, your driving 100,000 miles per year only nets your $30,000. To someone who has been making $10/hr, this is good. But to a former factory worker that was earning $16 to $30 per hour, plus OT plus benefits...this is a major adjustment.
But the economy keeps churing out people that can't get a job, so they turn to trucking where they get 'free' training and 'an exciting career in transportation'.
The transformation for so many of these displaced workers is so shocking and hard that most don't or can't stay.
One of the ways for these workers to stay in the industry is to find a local job. So what we have are thousands of drivers looking for a local job in a market where dozens or possibly hundreds exist.
The companies with local jobs don't have to offer training or school. They don't have to accept newbies. They have a line stretching around the block of qualified and experienced drivers wanting to come off the road.
It's true some companies will hire newbies. You have to search hard for them and there is a great deal of luck. I had a younger brother that got the state to pay his CDL school costs under the Displaced Workers Act. He decided he didn't want to go OTR and all my older brothers (also drivers) and I could say was, "Good Luck!"
I'll be darned if he didn't land a job pulling a propane tanker two weeks later. Home every night. But his timing was perfect. The guy had just lost another OTR driver who walked away and decided to try 'a fresh face' so he could train him his way. Joe just happened to walk in the door an hour after the last guy quit.
Timing and Luck!
So the jobs are out there, but they are hard to find and require some luck. But they are out there.
So it is possible to get your license for free and get a local job. But I don't see it happen very often.
OTR is the training ground for most drivers. It's where most experience is gained, largely due to the training companies running drivers thru the grist mill to keep their costs lower and deal with competition.
BTW, training companies make a lot of money off government 'retraining funds', so there is an incentive to march the masses thru the system regardless of qualification or any real vetting process. If the government were to take those funds away, those same companies would be required to pay a lot more to keep good qualified drivers and we would end up with the OTR being the top of the food chain (as it once was) rather than the bottom, as it currently exisits.
Hope this explains things a bit for you.
Good luck in whatever you do.

Emulsified nailed it.

thanks fro the lengthy yet informative answer :P

I had a younger brother that got the state to pay his CDL school costs under the Displaced Workers Act. He decided he didn't want to go OTR and all my older brothers (also drivers) and I could say was, "Good Luck!"

The lady at my local "Jobs Center" told me they aren't allowing anyone to file WIA/DWA applications for CDL anymore because no one was getting a job local without going OTR first...and no one wanted to go OTR. So now you have to COMMIT to going OTR before they'll even consider you for a grant to pay for CDL school. Lesson learned. She said somone comes in everyday asking about CDL. (Are you better off than you were 4 years ago?)

BTW, training companies make a lot of money off government 'retraining funds', so there is an incentive to march the masses thru the system regardless of qualification or any real vetting process.

I keep hearing this here, but no one can say what the mechanism is. How do starter companies get paid by the government to hire and train newbs? I've never heard of any legislation or bills for this.

The State will help you with training they put u in a driving School to learn BUT NOT ALL STATES do this.

Keyster, most companies that hire you after your training from the WIA will require you to be an OTR driver. You will get low pay with starter companies who will require you to be in a contract for one year. If you quit or get fired within that one year period then they can hold you to a certain dollar amount that will be paid to them for hiring you after getting out of school. Once you have your one year period in with the starter company, then most companies will bump you up in pay or you may just want to look for a company that better suits your needs. I highly suggest that if you go to school, and get your CDL to be prepared to be away from home for 2-3 weeks at a time, but there are some companies that hire student drivers that will have you home on a weekly basis. This doesn't mean that you will get home every weekend, but you would be able to be home some time through the week.

If you have little one's or a significant other then it is very hard to adjust being gone for long periods of time and can put alot of strains on a relationship. If this is what you truly want to do, then I would say go for it, but you need to realize that you will have long hours and low pay for awhile until you get the experience behind you.

Thanks mama.
I was aware that regardless you must go OTR, but my Unemployment Office wasn't until recently.
My point being that even they are screening people for OTR capability, because their research showed that WIA granted guys were refusing to do it after the fact and remained unemployed.

Once private school is paid the starter companies don't have you under indentured servitude, that's only if you go to their training "academy". The other option is you pay for school out of pocket and the starter company reimburses you, but I believe that does generate a contract if you quit before 6 months or a year, then you have to pay them back what they reimbursed; could be wrong.

I have no one at home and looking for some adventure out there.
I would not do this if I had family and/or was desperate for money.
My goal is one year and then re-assess my options.