Route to experience

Hello and thanks to all of you who contribute to this site. I've learned a lot from it already.
But, I have some questions:

I understand typically new drivers gain experience thru one of the big OTR companies.

However, I can't do that because I have 3 years before I retire from my full time job. I don't want to wait that long to get started.

So, here are my questions

1. If I get my CDL, is there much of a chance I can find an O/O who will train me so I can qualify to get a job in 2-3 yrs?

I'm assuming the short answer to that is no. So, here's my next question.

2. Would it change anything if I was willing to pay the O/O's increased insurance cost and was willing to drive for free?

Thanks for any info. you care to provide.

Hank,
NW Florida

 

Thanks for the timely response. I'd like to get a regional tractor/trailer job. Locally SNL is a good company with dedicate routes delivering bread from a big bakery in Thomasville Ga. Something like that is what i have in mind. I figure I need to make $35k or so after retirement and I'd like to work close to home. Does that answer the question? Thanks