Am I wasting my time?

You'll be fine getting a driving job. Seriously, don't worry about it. Get your CDL and the rest will fall into place. I know from experience that a sketchy work history is the last thing a brand-new driver needs to worry about. "Self-employed" is not a problem. I had a completely unverifiable history when I started out. Good luck, driver.

 

There are phones and computers in Canada. I very much doubt any company would demand to see a visa of you told them you worked in Canada fixing stuff for the last 9 years.

Unless the guy you worked for won't write a reference for his daughter's ex-boyfriend, at which point you might be in trouble.

 

Get some references. Hell, make some up.

 

They may not need convincing, they may just need documentation for their files to say that they complied with DOT regulation.

Whether they will bother verifying that document is another matter. Quite a few people have said that their previous employers and references were never checked or contacted.

Have a friend that knew you were in Canada, write a letter stating so. There doesn't need to be any detail regarding visas or unpaid income tax. Just that you were where you said you were. It wouldn't be a lie and if they thought it was, let the company decide if they will accept it or not.

What you are doing now is trying to guess what they would find acceptable. Don't try to do their job for them.

 

Send me a $100 then tell them to call me and I will tell them what and outstanding employee you were.

 

If you can pass a DOT physical, you're hirable. Your age is a positive asset in trucking. Trucking companies like older more mature employees unlike the rest of America's employers.
Sage is a good school and you must get a DOT physical to attend.
You will also need an original birth certificate and original social security card that's not laminated.

 

I used some friends who could be trusted to sound professional way back when I had that same problem. None of them were ever called. But if they are, you want them to hold up and provide consistent information.