Class A/Class B both have the same problem: A Skills Test where you bring the skills test vehicle, i.e. a truck and trailer with the trailer over 10k lb or a truck over 26k lb. I have neither.
Which makes it sound like I have to go through some sort of formal for hire training class/school, don't know.
Thoughts?
This is the issue you will run into. To get the CDL, you must have a CDL job and qualified vehicle. If the vehicle you use gives you restrictions, those will limit the jobs you're qualified for. A truck driving school is more focused on OTR, but will get you the ability to check all the boxes (even some experience).
This industry is so heavily regulated, it isn't going to be a good retirement job, for someone out of their element. The truck driving also requires a Medical Card. Other requirements may apply, based on weight and distance. If you're near a State line and not in a Commercial Zone, hold onto your lugnuts....it's going to be bumpy. All of this costs money, in one way, or the other. Another plug for a school, if you don't know the regulations on tie-downs, log books, permits, mud flap requirements, inspections, etc.
How you are thinking this will go and how it is are not very similar. On the surface, it's simple. The machinery isn't overly complicated, it's fun to have a job where you have accomplished something, and it's work that always needs done. In reality, liability insurance for an employee to dig under my company name is going to cost more than I can afford to charge; especially, a part-time one. Workman's comp, liability insurance, DOT regulations, etc are all based on full-time employees. The minimum for Workman's Comp assumes an annual salary of over $30,000. For me to hire you, and pay the required operating expenses, you're going to have to do $1,000 an hour of work for a full time person's $100 per hour. Then, if you quit, the pro-rated amounts are still going to screw me.