Aspiring Truck Driver

I've been reading thread after thread, some great information so far. I want to get opinions on what my first move should be.

Short Background: I'm 27 years old, male, veteran of the United States Air Force (I was a Crew Chief for KC-135s). I've been unemployed since November and living in transitional housing for veterans in Atlanta, GA since that time. I have two good jobs waiting for my background checks to come back. Finally, I am in a pretrial diversion program for shoplifting from Kroger around the same time I entered transitional housing. I was hungry and well, I stole food, sounds like a Charles Dickens novel but its true. On March 3rd I will have my charges dismissed, as of this post I only have 3 hours left of community service and I have to pay my $200 dollar participation fee and take a $65 anti-theft class (yeah that's a real thing..). So no convictions, one arrest ever floating out there in cyberspace although with pretrial diversion my official record will be clean and unemployed since November. I have also been sober since November and am proud of that. I was drinking too much and smoking marijuana.

Additional Note: Since the Air Force (2011) I have held one job for a year and worked for temp agencies in warehouses. My gaps can be explained by going to school and not having the need to work because I was receiving a stipend. I did not lose any job due to alcohol or criminal activity.

Questions:
1. Considering my background, I am weary of the hair follicle test *crotchety old Nixon supporter shakes cane in disgust*. I have been clean and sober for almost three months but I am aware that the hair follicle test can go back 12 months. What companies do not perform the dreaded hair follicle test? Or if I let my recruiter know my situation ahead of time, can they make an exception for this millennial snowflake *cherub blush*?
2. So, if my background and everything isn't an issue. What is the best company to start off for? I will need to obtain my CDL A (I can use my GI Bill for this but I will need experience so I think I might want to just get trained by a company). I have given my information to cdljobs.com so far and received emails and phone calls from CRST, Covenant, Swift, JB Hunt, Stevens, and a few others. From my research none of these except JB Hunt seem like good places to go. Note, I want to solo, I absolutely do not want to run teams beyond the training phase. I'm looking to make 500-1000 a week once I am hired and running solo. I do not require much home time, I understand that I will be on the road a lot, this does not bother me, at least not for a year or so.
3. Will I finally be able to wear a trucker hat without being a hipster *insert name for female cleansing product*?

 

How difficult is it to get hired on with a decent company with a CDL A from a private school, without experience? I also was reading up on Prime and it seemed as if it didn't matter much if you got your CDL A already, you will have to go through their training program if you do not have experience.

 

Ok cool, thank you! I have heard good things about Magnum and will be calling their recruiter today. I also have the option of public funding of my schooling due to being a veteran and living in transitional housing. My program can pay for me actually though I need to check up on their school. They said it was only three weeks which seems kind of sketch.