Profile For Aspiring Driver

I'm going to be boldly honest here.

I'm a single man 35 yrs old without a real work history. I worked for years doing home repair and refitting for rental properties, I've put down tile floors, interior painting, plexi-glass windows, did evictions etc... I haven't worked for a number of years due to being on SSI (alcohol issues) I didn't pay taxes when I was working for a number of issues, such as my boss not being a licensed contractor, but mostly because I was paid cash and I earned very little by working on and off anyway. I was extremely naïve about how that would limit me down the line. I have no real provable work history. I would like to get myself established in a job that pays a wage I can live on, and am considering trucking. I can swing the cost of training program like NA or all-state but I certainly can't afford to do so if I would be unable to be hired afterwards. I have spent weeks watching videos and learning as much as I can about trucking online and have found horror stories to freeze my soul, as well as inspiration.

I have addressed my personal issues (alcohol) and it isn't a problem, i've been clean for quite awhile. I have no ties to prevent me from being on the road for a month or more at a time. I am overweight but I have no reason to believe I couldn't pass a DOT physical. I've had 1 speeding ticket in my life and that was about 3 years ago. I took out a utility pole once but that was like 10 years ago, other than 1 parking fine that is the entirety of my driving record.

My largest concern is my lack of employment history. I don't want to plop down 4 or 5k on training to find out I've just thrown away all that I have. If moving forward would be a waste of time (and more importantly money) I need to know it, as well as any suggestions anyone may have that could alleviate those issues.

A more positive note, I have to say i'm sure i'm not the first person to seek a possible career of a transient lifestyle due to limited options. If my lack of work history is unacceptable then how long would I need to work as a taxed employee stocking shelves or whatnot?

If i'm just being a pie in the sky dreamer I need to know it.