"I am interested in starting a trucking business."

Back in the early 90s, I had a friend that was given $100k from his father to start a coffee shop. It was the only coffee shop downtown (there wasn't another for 15 years). The shop was a major hit. People were lined up around the block every day. They opened at 0600 and closed at 1300, M-F. Hugely successful.

After a month or so, my friend shut the coffee shop down. Why? Because he didn't like having to get up early in the morning. "I'm not a morning person, Six."

If I were opening a coffee shop downtown, when would I expect for my busiest rush to be?

This is what concerns me about your post:
After reading through all of the horror stories about trucking companies and seeing so much toxicity on forums and elsewhere I was starting to get biased against the idea of being a company driver.

There are lots of guys who come in with the same idea and the same questions as you. Why do they want to be an owner operator? Because of the horror stories they've been listening to. You mean you've never heard any owner operator horror stories?

Why do you want to be an owner operator?

I had that asked to me once. I was a company driver, in the top 3 of 2500 trucks, making $2k/week. Were there horror stories? Sure. In fact, I took over the payments of the truck of an owner operator at the same company who was 6 months behind on his truck payment. How's that for horror story? Well, I took over the payment and notified the company and they wanted to talk to me and school me on the in's and out's of being an owner op. So we all sat at a table and they asked me why I wanted to be an owner operator.

In the horror stories, you hear about the dreaded lunch counter, the stomping ground for the supertrucker, the end all and be all of trucking, been driving since God was talking to Moses and has pulled every load known to man and knows everything there is about trucking. Sit there. You will see some fool come in and tell you about how trucking was in the good ol days and that now, trucking is no fun and that 'we can't make any money anymore out here.' Don't speak, just listen. Within 5 minutes you will hear drivers tell you why they don't make money and it's almost always self-inflicted. "I dont go to the northeast. I don't run at night. I don't drive in the rain. I park as soon as I hear the word snow. I'm in Wisconsin and there's a hurricane heading to Florida!"

I remember strapping down a load at a shipper and a driver asked me where I was going. I told him northern Alberta. He wanted to know where that was, and when I told him, he shook his head and told me how he wouldn't go there regardless of how much it paid. That's good to know, hand. I wasn't going to bother to tell him how much it paid anyway.

In the open deck world, it's the dreaded tarp. When they start talking about tarp, watch the sidewalk sissies shudder in fear. When I was a company schmuck, I tarped. It didn't pay much then. But I was learning with their tarps. With certain loads, if you mess up, you will ruin a set of tarps. You do not want to mess up a tarp job on a high dollar load. When you're in a company truck, pulling a company flat, they beat the regs into your head. You will tarp and tarp and tarp, and when you get done, you will tarp some more. Oh, and you STILL have to drive. The owner ops do not have to tarp. They are not taught how to tarp. But, how hard can it be? Yeah, it's just like wrapping a gigantic Christmas present with a 150 lb roll of wrapping paper. Oh, and the wrapping paper has to withstand 70mph wind. Do it wrong, and you ruin a set of tarps and risk a claim on the cargo.

The lady asked me, "You do well as a company driver...why do you want to be an owner operator?"
Because I am leaving too much money at the table.