Which setup ?

Get a tractor trailer type situation.

If you tie on a pup or even a doubles with a pintle hook Your skill level needs to evolve beyond expert to manage that trailer as it sits in it's own physics world able to roll over when breathed on too hard.

Nice and steady, easy does it. It will be a while getting down. That trailer is plenty.



Here is a couple difficult ones with pups included.

 

What are most using in your area?
What are you experienced at driving?

 

Ive been off road with a cement mixer loaded to around oh... 60,000 pounds plus.

Now the mixer I had specifically had cross rib drive tires so that no matter what, if at all possible you will go forward or backwards. However if its raining or snowing? You have zero curve traction. Obviously not absolute zero but if you abused it back there she will spin on her forward axle and try to kill you or a family.

I could never take a loaded highway tractor at 46000 where I managed to force my 60000 pound cement mixer offroad.

I remember one situation I was on a common road on top of a ridge lengthwise. Call that 30 feet apart. Cliff dropped 400 feet on the right. Houses 60 feet below pavement on the left with backyards going vertical against the next ridge over follwoing our ridge but higher and bigger and steeper. Such as Ozarks.

To get the loaded mixer down off he common road into the man's driveway required the spring brakes to be pulled 1/4 of the way down. She then slides deadweight until reaching the grass off the end of the drive pad. The slope would be estimated at about 52% and a spot about 15 feet short of the common pavement itself is actually 80% for 6 feet.

4x4 pickups can climb that easily. Easy up and over. And thats pretty much all the home owners on that road drive. Power strokes. And a number of light 300 cummins actually on manuals.

So Ive slid to a stop on this man's backyard. Grass is a little brown and the ground is solid dirt. Perfect.
K turn the truck and back up to the designated swimming pool to be poured.

Empty. Wash everything off Walk the chutes up to the common road 60 feet above your head. Examine the treetops of those around your Mack Mixer Truck from the pavement after you have stacked your chutes. (Ride up is expected to be extremely rough you load the chutes as soon you reach the pavement.

Put truck in third low range, what I would call full lockers on and stomp it with the drum off.

You are doing 20 halfway up and see nothing but sky. As soon you hit that last 10 feet you get a horrible bounce. JUST BEFORE your wheels left the ground, you slam the service brake with your foot FAST and come off it FAST She is in the air by then.

About 8 feet up in the air and plop down on the pavement with the front bumper overhanging the drop on the other side. Since your service brakes are on again you stop instantly with a little slide. Maybe one of your steers is dangling over empty air.

Wipe bloody nose and tend to your hurts With a 5th of bourbon and a rag. Take a swallow for your nerves. Drain and toss bottle for the angels share to have.

Take a walk around your truck to examine spring hangers first, U joints next followed by Cab and drum mounts then work your way down. Load chutes, hop in call off the job on the radio.

Then promise to God and all the world you will not be back up there ever again.

And the truck did a good job even though you abused her a little bit And the boss does NOT need to know about those flying trucks.

 

Ok, in one day my truck can be either one. I have a long wheel base log truck and a set of bolt on bunks, and a pup if I need to haul short logs, and can switch from it to a regular western long log setup in a matter of hours. I do not do the pup thing much, and never in the winter. The log trailer pulls much better in snow and I can back it back down the mountain when I spin out, or slide down, with the pup, you are in trouble quick.

 

Another thing about a pup, when I first rigged mine for short logs, I did not build a trailer ride, so had to pull the pup back empty. in my opinion, this is not good for several reasons, one is you barely have to touch a brake and the wheels on the pup are sliding, second, is you have no driver weight, and when we even got a light rain on the log road, I would spin on some of the grades. I had to build a trailer ride, so I could load the trailer on the truck when empty to even get up some of the hills.
third, the landings for the most part were not built to turn truck and trailer around, so we had to get creative, until I built the trailer ride.

 

Before I would spend that kind of money I would drive for another company
for awhile. You can get a lot of real life experience......keep track of expenses, etc.
Figure out what kind of rig works better for what you want to do.