Possible side job

Keep your company job. Take it from someone who has made a living with an old truck for almost 20 years. Your chances of matching, or exceeding your current income driving your own truck are slim to none. If driving an old Pete looks like fun to you, buy an antique and take it to truck shows when the weather is nice. I can promise you will have a lot more fun, and have a lot more money in the bank when you reach retirement age.

 

The boss has a per mile rate worked out.

 

HOS are an issue even if part-time job is cashier at hardware store.

 

Buy it and restore it. Maybe put it in truck shows. When you retire then maybe put it to work. If you try to do anything trucking "part time" I guarantee your wallet will be sucked dry.

 

The HOS would kill it. Stick to your day or night job.

 

You might want to study up on federal HOS regs before starting your own trucking company.

 

Are you sure you'll find work each Saturday? Short enough loads that you can complete the same day? Do you know who you'll lease to? Why not talk to your company about leasing to them? If you're making 6 figures now, maybe they have some really good rates that they'll pass on to you?