Ride Along timeline.

I personally would recommend working a tad harder to find a way to get your schooling done at a school not run by a trucking company. You will end up "owing" them. Most will want you to sign a year or two contract. And if you have to leave them before that contract is up you will owe them more than the school was worth. May not be your or their fault you had to leave, but you will still owe them. Also, if you cant afford to go to school, you are gonna get real tight on money soon. Most new guys only make 30 thousand in first year, if they are lucky. you may not be able to afford to stay with them long enough to fulfill the contract.

 

As for passenger policies, it varies a lot. Some companies you can take passengers from as soon as you go solo. Some you never can have passengers. Some allow family members as young as 5, some they need to be 18. Some will allow friends to ride with you, most will limit it to immediate family members. And some charge you so much a week to have a passenger. Just talk to recruiters till you find one that suits your needs.

 

Since you're a vet, did you check this :

VRAP

WIA

Google for more info., both programs will pay for your CDL school.

 

You sound like a really nice kid. All the Marines I know finish whatever they start. I am sure you will do well wherever you land. Trucking is hard enough without the added heartache of a substandard company.
A pell grant will pay for most of your schooling. A student loan can do the rest. The rate of par back for the loan is no greater than what the company will be chopping off your check. Have a dozen companies come looking for you! Recruiters will swarm to the school. Talk to your instructor about the sales pitches. Learn to sift through the bull. Earn more money.

Now to get back to your original topic. You want a rider to go along? I am sure you can arrange for that with any company. Talk to the recruiters.

 

For newbies I think Prime is a good starting company because they pay higher than most companies. From what Ive read about them, they have a great training program. My opinion about Swift is alright but there are better choices. With Swift on your first year you will have a hard time and their school is really serious. But your instructors will work with you and teach you everything you need to know to pass and get your CDL but you need to work with them. I read positive things about Roehl and I would recommend a newbie to go with that company. Now there is more options available. Companies I recommend for newbies are Prime, Millis, Central Refrigerated, Roehl, Stevens. Companies I wouldnt recommend are CRST, CR England. If you get your CDL on your own it should be better if you can because you have more options. You would be able to go with companies that pay higher like Crete, KLLM, May Trucking. But in those 3 choices you mentioned earlier Prime should be the choice because the way their training program works and also a higher pay than most training companies. Than Roehl and Swift would come after. Look at other companies to and do more reviews

 

You should concentrate on getting your CDL, a job, and plenty of experience, before you add a "rider" (distraction)