I owned a 69 1/2 chevy with a 250 sm465 and i pulled alot of stuff with it. The heavyest was a 84 C30 with a 12 foot refer bed.I used a tow bar and pulled it for about 150 miles. I now have a 67 GMC that was a 250 4 speed 1/2 ton. I pulled a gooseneck with 3 cars on it several times. This was before thay raised the speed limit. I liked the 6s alot and before i moved i had 20plus 250s and some 292s. My 67 now has 3/4 ton axles and a 350. The first 3 trips i thought the 350 was a joke. I was down shifting alot to make the hills. The next trip with the gooseneck i drove like i was mad keep the rpms up and it pulled like a freight train.I would go back to the 250 in a heart beat if they lower the speedlimit. I dont think the 250 will ever do what you want. I know you dont want to hear this but a 350 would be better.I would like to know more about runing a 292 with a overdrive because every one i have had was a gas hog so i dont plan on useing one agine.