Where to start when entering the trucking industry?

Nobody is going to put you through CDL school, if you have your CDL.
Just training.

 

There are people who take advances, even when they're collecting the training pay. Talk about stupid.

 

Almost all of them will insist on doing their own DOT medical exam and card. Don't worry about it now. Unless you think there is something that might be a problem. One that you can do something about, between now and then.

Best thing I can say is. Put in tons of applications, everywhere. Find good companies, and apply. Look everywhere. Linkedin, Indeed, craigslist, news paper, state employment board, this sites job forum, other trucking sites job listings.
I did, I have a job, and still have them calling. And I just graduated CDL school today. Just got my license yesterday. If this one job doesn't work out. I've got two other good ones who told me to just call up.... they'll tell me to come on in.
I still would suggest Prime. I like them.

 

The company you choose may want you to get a physical from their preferred doctor or they may want you to get the physical where you now live and bring the paperwork to school. The company will tell you which and you can also ask.
CDL Permit - ask the company if they want you to get a permit in your home state or wait and get a permit in the state where the school is. Start now studying for the CDL Permit tests.
Google : Free CDL Practice Tests Vermont. There's also an app. "DMV Genie App-cdl practice tests."
Concerning the practice tests; memorize the answers word for word. That's one part of this that's changed since you went to school. You must know the answers word for word and some states the wording is different. For example, "air indicator" or "air guage", even though they're both the same, some states will mark an answer wrong for not using the correct work that particular state uses.
It's not that complicated, so just ask the school/company which state they want you to get the permit from. For example, if they say Missouri, then you and your classmates will do that together, no big deal.

 

If he lives too far out of their main freight lanes, they will require him to lease a truck. That's been discussed on here many times. Prime won't pay for fuel for him to go home for home time if he's too far out of the freight lanes. If this is the case, after a few days at home, his next paycheck might be a negative, because of deductions for fuel and the truck payment, plus whatever else he's paying for to lease the truck.
If he's interested in Prime, he should ask questions about this.

 

You're correct; as long as your physical is up to date, you're good to go. Just ask about the physical and if the company wants a new one from their doctor or not.

 

CDL with zero experience trying to figure out what to do next to get into a truck....

You need a training company. The training company needs you to 1.) be able to pass a DOT physical when you get there 2.) drive a truck around the block and down a road BEFORE you ever see a trainer. Can you do this? Are you for certain? I would get my own dot card. Yes, I know that odds are you will have to take another, but I like to make absolutely sure.

Can you redo that drive you did when you tested out for the CDL? Are you certain? Half of the people that show up for training are going to get sent home.