Waste of time/money?

I've been thinking about trying to get back into the driver's seat, I'm just not sure if I should try it now or wait a few years for some things to drop off.
I got my license through one of CR England's CDL mills in 2011, fell for their lease driver shtick, wasn't breaking even, so I quit and found a local doing food and tobacco delivery for about a year before I moved on to Schneider on the Family Dollar account(YIKES!). Over about 6 months, I racked up 4 non recordables on my DAC. I'll cop to two of them, the other two I will be disputing. Number 4 was what got me fired, a "Struck overhead object" which was hitting a tree limb hanging over the road, which I misjudged how low it was. They let me drop the trailer at the store and drive the tractor to the yard to empty my belongings and pick up my car. On the way home in my car, pissed off, I racked up a 70/35 speeding ticket. Having a Challenger made it too easy. I know that normally comes with a reckless, but I
guess the cop was merciful because I had no citations for the previous 6 years, it was relatively rural, and I was clearly distraught.
I was only able to get a temporary job delivering landscaping rocks/brick and plants and after that was over, I surrendered my CDL because I couldn't afford a sleep study.

I was in a bad place in my life at the time, but there's no excuse for being so stupid apart from maybe needing some better training.

I've changed and grown quite a bit in the last few years, thanks in no small part to my wife and son, who were not present at the time. I need to give them a better life and this is by best chance. I don't need to hear "maybe this isn't the industry for you". In the past, sure, but now I believe it is.

So the plan is to go to truck driving school again to refresh my skills, but a real one this time, through the community college maybe. I work in fulfillment for a major online retailer now and they give us Restricted Stock and offer Tuition Assistance up to $3000/yr . I'll have 4 RSU's vesting in late October and I can start the tuition program at any time. The only hesitation I have is because of the big ticket and DAC dings, and the sleep apnea test to get my med card(that is a minor concern, I have insurance now). I talked briefly with a local law office about the MVR and they said while it would have been better for me to get a lawyer when it happened, we could probably get it expunged or at least changed to something like a seat belt or insurance ticket because it was coded as an ordnance violation.
The other option is to wait another three years for the incidents to drop off the DAC and the ticket will drop the details on my MVR.

 

The ticket is most definitely my biggest concern. I know at least two small locals that will hire me if I can get the ticket knocked off and get the CDL back.

 

Yep, the trailer got a hole in it. Missed the tractor. I never figured that part out.

 

Paltry. $13.40 hourly. Mostly 40 hr weeks, overtime is rare at my site. Probably averages 29k, plus I have insurance and 401k. So match or better, which I know is easily doable. As for the sleep apnea thing, I don't think I have it, I sleep well, but I've gotten fat and had a big neck even when I was in shape. So I know they'll want me to test.