Ha ha. Token...they must have some seriously wuss trucks out your way. I guess we can rack it up to Cali emission standards? LOL Sooo just kidding!
BM newbie, but trucks w/ ass is most def my wheelhouse

Don't get me wrong, a dually is definitely optimal, not absolutely necessary, but optimal- especially for long hauls.
The pics below are when I went to buy my crawler/loader/backhoe. Ohio to Maine empty, but then back to Ohio, through the Catskills no less. 4000lbs for the trailer, 8000lbs for my truck, and 16,680 for my crawler. Total GVWR 28,680...through the mountains. Yes, I was a wee bit overweight- shhh, don't tell anybody. And I drove slow as mudd to be safe.
To be clear...I do NOT recommend this LOL. But I didn't just wing it either. Class VIII bed-mount, for either my gooseneck OR my 5th wheel hitch. Firestone helper bags. 4.10 axles and a 6spd manual which deeefinitely helped down the hills, mostly in 4th gear. And of course, the bread winner and holy grail of diesel engines, the 7.3L International. (yes, the 5.9 Cummins is nice too lol)
Trey- it's doable. More than doable given it would be 5,000 lbs less over flat-at-as-hell ground. I have a post in this section "Truck or TDI" and was gonna bring my gooseneck out, but didn't have a need. And the fuel cost difference between my truck and my TDI (@50mpg) is maaaassive. At 15mpg and 2306mi Columbus Ohio to BRC and back, we're talking close to a grand, just in the diesel fuel.
Your predicament has me way curious, but I think I'm too far logistically to make what total costs would be (fuel & maint) worth your while.
Flint