Have cdl. no air brake no gears no way I want to spend 4k

So heres my situation.
I work in the used crosstie industry bundling and loading out railroad ties. Have been since 88 with a 13 year sabbatical in Alaska. Id say at least some of you flatbedders will know what I'm talking about.
Its time for a change, says the back.
I have a minimal amount of experience in a 10 wheeler boom truck, just enough to say, yea OK I know what the inside of a truck looks like lol.
I've been pulling a streach dually with a 30' goose neck for ever it seems like. Last year I had to get my class A at the behest of the Missouri dot. Nice guy though, 7 warnings 1 ticket for no app. Tags. Didn't get gears or airbags because the truck didn't have them of course and the company wouldn't roll the boom truck over for me to use.
I travel 24/7/365 anyway and want to go otr. However having loaded more trucks than most of you have hauled loads. Having a better than average "newbie " prospective of what's involved driving truck and many many miles under my belt in every weather conditions I have come to the conclusion that with this cdl and no experience I am the proud owner of squat.
Thought about buying a rig and going o/o but more than 5 mins thought on that....well shooting myself in the foot seems like a smarter choice.
Swift wants me to start over at 4400.00 for the class and pay them back. Uggg
Is there a question here you ask?
Well, yes. What would you do in my situation, after you take away your contacts, friends, and paycheck

 

I'm in Minnesota now but would probably go to Missouri if I have to go to school as the wife's family is down there.
The kind if driving? Otr, travel around take the wife kinda driving. Wouldn't want to do in town routes till I'm as good in the rig as I am in my pickup.

 

Once I learn the ropes I'd be interested in all the endorsements. I can't see anyone hiring a greenie to drive hazmat, but I've been wrong before. I here tell reefer and drop deck anr the money makers now.

 

I was hoping to save that 4k but yeah, I agree, 0 experience.