Trucking vs. Military

My advice is a bit different than everyone elses. Ask yourself if you truly want to go into the military, and drive otr.

I think you want to do both..... So, go for it.
Why not go to a good trucking school, then go into the National Guard. You are going to be unable to take online classes in boot camp, or while you are out otr with your trainer, so plan in advance.
But, the guard is only for a weekend, until your governor gets a wild hair up his rump, and has you deployed..... but I think you very easily could do both, if you really want to. Just keep in mind you have 70 HOS(hours of service.) So your military service will count against part of that, but if you're in the guard, then that's only one weekend a month.
Oh.... I don't know about all states, but when I was fueling up in Kansas a while back, I was in line with a bunch of the Kansas National Guard..... An NCO, at the fuel aisle next to me, kept trying to get me to join, even though I lived in Kentucky, or Colorado, or where ever I lived at the time. lol
He said you start out as an E-1. That's the bottom of the barrel in the military..... an E-1 for someone with a CDL? I don't think that sounded worth it to me.
Just remember one thing that rings very true about the military, as well as the trucking companies.... NO MATTER WHAT THE RECRUITERS IN BOTH INSITITUTIONS SAY...... DO NOT BELIEVE A WORD THEY SAY.... UNLESS..... UNLESS.... YOU GET IT IN WRITING.
Talk to people both in the military, and in the trucking industry who are doing what you plan on doing..... and remember, they may be biased, so take everything with a grain of salt. You may have someone who hates their job, but if they think they may get a bonus to trick you into joining them, then they'll lie out their teeth.
Hope I've helped a bit. Just remember the getting everything in writing, and all recruiters from the military, and the trucking industry are liars part, and you will do fine.