Asking questions here is your best start, and welcome to CAD. (Mud buggy... cool name)
IMHO, I think you are back where you belong, in the country, and with a good secure local job. You should take up hobby to keep from getting the urge to wanderlust.
OTR driving will suck more than the cake job you have now.
But being you have no ties, you can go live the trucker lifestyle, and you may very well enjoy it. I did, and many have as well.
We are just always shocked anyone would consider themselves willing to drive through the 7 circles of hell, if they don't really have to.
I think you would have to have some kind of refresher school training. Your driving experience although class A, won't be considered much on a National Co. OTR application.
You might hire on one of the local O/O OTR companies in your neighborhood, so maybe talk around with some of them, first.
BTW, it's okay being crazy, ... it's an OTR prerequisite. I'd put in on the application like a doctorate degree. Tell them you are a Road Scholar.