My truck pulls like crap but I attribute that to a few things

Bad alignment
No swaybars
Worn springs
Spongy brakes

 

You mentioned your truck tires, what about your trailer tires and bearings. Age of the tires, properly inflated? Last time the bearings where checked/greased?
Just a friendly reminder, I've seen too many people (one is too many) neglect these things and travel hundreds of miles from home and can't safetly get back with their trailer because they didn't grease their bearings in who knows how long.

I have had 2 tires on my trailer come apart, the first one I caught before it shedded the tread after bringing a truck back from NY. The 2nd one the tread came completely off on Rt. 17 in NY bringing back my brothers '96. Good thing my dad carries jacks with him in his truck.

 

the most ive pulled gross weight 30000lbs thats 6000lbs for truck + 2000lbs for trailer so 22000lbs loads not bad hey
on the pic here ive got 1800 on truck +9600 on trailer https://www.dieseltruckresource.com/...cat=500&page=1

 

Listed to JD ..... trailers are all-too-often neglected in the seasonal maintenance routines. Good brakes on your truck should be able to stop that load, so I wouldn't sweat it too much if the trailer brakes are a little shakey. But tires and bearings ... let alone springs / bushings ... if it's been awhile since you've used the trailer, I'd say take the two hours to pull it all apart, clean and repack everything.
With that kind of weight, pull that car darn near the front of the trailer - until you see a good bit of settling in the rear of the truck - a few thousand pounds does wonders to smooth out the ride of these old machines. Especially if your trunk is full of engine parts.

My personal record (followed by a loooong lecture from my local weighstation operator) is 36,000 Gross. 12,000 on the truck and 24,000 on the trailer - haulin 450 small square bales from Upper MI down to Chicago (350mi each way). Managed 45 - 55mph most of the way. The poor deer that sauntered into the road was not much more than hamburger when the last of seven tires rolled her over....
Threw one other pic in my gallery just for fun ... home-built trailer (truck axles under a beer-delivery truck frame) loaded down with the 'wheelin toys, in their early days (read: college budget). Enjoy!

 

Most I've pulled with the old truck is about 20k or so. That was about 12k loaded on the trailer in my gallery which is about 8k empty. Anymore than than and I use the newer truck. Used to have a 32' bumper pull side dump bale trailer that I would haul 6 1-ton bales on, so that was about 12k, the trailer was about 3k, so 15k total on a bumper hitch. That was alot, around the farm it was no big deal, at 60 mph the front end got a little light! Of course you guys probably think I am nuts, and your probably right!

 

Be careful in the turns if it gets slippery out. Rear lockers in rigs towing heavy loads can get a bit squirrely. The pushing of the trailing when slowing down can make the locker lock and unlock at funny times. If you are going around a slppery corner at the time it could get interesting. You've got barkes on the trailer right?

 

JD730, nice load, is the back tractor a early '40's G?? Is the front one an A??? My Dad and a I have a few, but the gooseneck we currently have is only long enough for one tractor. Our trailer weighs about 3500lbs. and our GM with the wide front weighs about 6000lbs.

 

Exactly, the G is a late 1941 and the A is a 1936.