Questions regarding equipment and laws. Long Read

Or ignore X1, as he's full of it mostly.
Like @not4hire said simply log it as off duty. You will loose the 8/2 split option, but that would be all.
Get an air bed and if you are comfortable enough to sleep, go for it.

As for the truck, my suggestion is drop the 4x4. It just causes more problems and you will likely not be delivering to many mud lots anyway. Also, the engine is more of a concern than the transmission, mainly because for the new Rams there is only one transmission matched to the Cummings. And let;s be honest, the only reason the get a Ram is for the Cummings. As for the extra tank, I would see what it's like a few weeks without one, but be prepared to get one.

Trailer: What makes it a gooseneck is the ball, if it has a kingpin it's a 5th wheel. Simply match trailer to hitch. Don't have more advice as I've never done hotshot.

As for Drug and Alcohol, @Moose1958 don't you have a chart that shows what requirements are needed for a non CDL CMV vs. CDL CMV?

 

Govt is definitely trying to get rid of the pickup haulers no doubt. It would be an awful tight squeeze for me in the back of a 3500 to sleep since i’m about 6’3 190. I like my 78in aerocab on my pete though. I just couldn’t live in a pickup cabin for a week at a time.