How Strict Can Insuring A Driver Be?

I'm a recent graduate from Swift. I started driving around October of last year and ended my career in an unfortunate slow-moving jackknife that has landed me in an extremely tight spot. I have 4(four) accidents total with two of them being sketchy.

1st was a minor backing accident: It was test day and I underestimated my turn leaving the terminal. I decided to back right up to correct this just a little without noticing that the guard arm was lowered. I was told this would not be recorded since one of their instructors was the passenger and there were several other people who didn't bother to say anything but watch.

2nd was a right-hand turn incident: This one I can't prove that I wasn't at fault for, but I know for certain that I wasn't. I was running behind due to having to slow down by A LOT while moving through the Colorado mountains during a bad snow storm that nearly shut me down. I made it just in the nick of time with less than 15 minutes to spare. There was one trailer in the lot that I could take and I was not allowed to leave without one. I did a brief inspection and discovered a bent rim(The tire wasn't flat) and my rest stop was only across the nearby underpass. I quickly hooked up and slowly inched along the road making it with just a minute remaining to legally shut down. I reported the breakdown and was slammed with a right-hand turn incident months later that I was never given any acknowledgement over. I do blame myself for not covering my behind and being arrogant.

3rd was a clearance-related incident: Short and simple; I was puttering along a DC yard in Wyoming when my tires began to spin. I panicked and spun them into the mud quite a bit which result in some damaged fairings. I would admit that I was nothing but careless and had a nice swear-storm while trying to get myself out of the mud.

4th(the worst) was a slow-moving jackknife: The roads were too iced for me to be driving on going through the I-70 shortly after leaving the Wyoming mountains. I approached an exit decelerating to about 20mph and slowly applying the break. At the very last second, I noticed my trailer beginning to lose its path. I tried to steer out from under it, but ultimately was driven off the road. I didn't collide with anything but my own trailer and the muddy ground. Fairings and radiator were both damaged, but everything was still operational. I received a citation for this accident which was "Unsafe for conditions".

If anyone has experience with recruiting drivers with similar incidents please let me know how deep in the ground I am. I need a good reality check.