After being told by more than one person that it would be a problem finding insurance.
I got a quote today from Progressive $6156 per year for 750/100/10 the only gottchya was a 500 mile limit. $975 for a Bobtail policy with the same coverage + $5000 deductible comprehensive (they don't offer it any other way). Some of the companies are self insured or have group coverage available. (That wont help if you are planning to drive under your own authority).

I looked on truckers dispatch and found for my state (OR) there are 13 companies listed, many names I recognize from other lists.

Is it possible that although some of these companies engage in predatory practices can an O/O can get a reasonable deal from them?

5mouthstofeed,
Is it your neighbor friend that is willing to help you get into a truck?

Your best way to go, getting your feet wet, is by buddying up with an owner operator. Sounds like your neighbor may help you get in with the work he is doing?

You can't decide on a trailer until you know what type of work and loads you will be doing. You first need to set up some type of work for that truck, before even deciding to get a truck.
If you can get set up with another friend who has their own authority, your best bet would be to run under his authority for a while.
If a felony is a problem getting approved under someone else's insurance , then you can apply for your own. You will really need only the Liability part. Check around and call a few insurance companies. This way you can run under anothers Cargo Insurance. You won't need to get that until you apply for your own authority.

There's a commercial insurance called Capitol Insurance , which I find is reasonable.
They won't check your background records.

I'd stay away from Leasing on with these Large Trucking companies, for many reasons that I won't get into.

Hauling Agriculture is an easy way to get started as an Owner Operator.
And the insurance is cheaper too, because Agriculture is exempt.

I think your "cue" is getting back into hauling Logs, since you've already done it before. Theres a lot of that going on around your neck of the woods. And it is Agriculture too!
Work on getting your own truck. And from that point you can work your way up with your own authority, then being a company with possibly more trucks.
Keep your thumb up !
LOL