20 plus years removed from trucking

Well, yes and no. Being military, yes, they are trained for a multitude of jobs, I just feel, coming from a military background, they may be amazed at the lack of discipline and ethics, and public acceptance in this industry, and quite frankly, I feel, coming from a distinguished career like military, then "stooping" to trucking is a step down, sorry, I don't have much faith in the trucking biz today, and I've been around it my whole life, and never seen it worse. I know, why am I here, then? To give these people, that may not have all the info, a different perspective to make a better choice.
People think, "what a great way to travel, AND get paid",,,well, it doesn't work that way. Most the time, you are stuck on some God forsaken interstate, or truckstop, you simply can't go see "Mount Rushmore" in the truck, and companies have strict rules on bobtailing. It's why most new drivers quit within 90 days. Just the facts,,

 

OTR is an adventure for alot of drivers and they like it just fine. Especially if you don't mind being away from family and friends. Alot of em' put their stuff in storage and live in the truck and save money. Another good thing about OTR if your with one of the big companies is you can take your hometime anywhere in the country just about. I know, I did it!

 

I agree. The job is 80% frustration. The vast majority of 'places to see' have highway signs that say 'No Trucks'. Most of the places you drive by, you will not have time to stop anyway. You'll usually be aline, too, so although DisneyLand has truck parking, it's just not that fun by yourself.
Have you looked into the workcamping life? You buy an RV & do seasonal work in various tourist attraction locations. It's a far better way to make a living while traveling & even if you go it alone you'll still have other workcampers to go & do things with.
There's a Facebook group for this and an entire magazine devoted to it. Seasonal jobs are available year round and there are plenty of them.

 

Park at truck stop for some needed time off in an area you’d like to explore, rent a car or an Uber and go see what you want to see. The road is what you make it, just like any other job.

 

I think your expectations are very attainable.

 

That's an option, although, Uber is in trouble, and not cheap by any means, more for an emergency, and renting a car, no bargain there either. $100 bucks a day and I have to go 85 miles to get to the nearest car rental ( outfit in town discontinued rentals because of liability). It's ironic, because there is a lot of time where you stare at your floormat in a truckstop, and it's never near any attractions anyway, unless "Aunt Lilly's Gator Farm" has truck parking,,,

 

Google for "Rent-a-Clunker" and "Rent-a-Wreck" for cheap car rental.

 

with a good retirement package, I'd get a small camper and roam the US at my leisure.