Your Opinion of best used Pick Up for Towing

I would definitely be looking at a 3/4 ton or up. My preference is gas just because the cost of a diesel is usually way higher than a gas rig and repairs on a diesel can be extremely expensive.

We have three diesels in the family, all Fords. Two have the 6.0 and one has the 6.7. The 2004 6.0 that they bought new blew a head gasket at 75,000 miles last year and caused almost 10k in repair work. The 2007 was "bullet proofed" before her dad bought it but it constantly nickel and dimes him to death on everything. The 2017 has had no problems other than the "death wobble" but only gets about 10 mpg towing and the ride is horrible. It's a crew cab 4x4 with a hay bed on it with about 25,000 miles on it.

I'm not sure what $40K will buy you these days but hopefully you can find something that will work for you.
 
We generally keep our vehicles until run into the ground - still have two '95 pickups (one gas, one diesel, both 3/4 tons). Last car was a Subaru Forrester that the engine blew up at 351k miles.
The wife hurt her knee and couldn't push the clutch in. I was upset about selling the 2002 it was maintained to a t and the wife drove it carefully.
 
With that weight and I would also agree 3/4 ton truck. 6.0 Chev will be a nice truck that'll work well. Ford 6.2 or if new-new, 7.3. Ford 6.2 would tow good but none of these exactly run away with 10k behind them. I don't know much about Dodge gasser in 3/4 ton.

Diesel would make light work of that 10k.

Half-ton, I'd maybe (MAYBE) tow 10k on my F150 once if short distance, but personally don't think I'd want to regularly tow more than 6-7k of a camper.
I have a F350 and a Ford F150m with the 2.& eco boost and with the F350 I really feel the load behind when I tow the tractor the power is fine but with the 350 You can't tell there is the trailer. The trailer is about 1,500 lb and the tractor about 4,000 lbs. The F150 has the light frame.
 
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