The biggest downfall of a single cylinder set up is the low angle at start up. I have often thought about installing one or two short cylinders vertically at the front of the trailer to get the initial lift into motion. I have built two dump trailers and two dump bodies on F350's, all dump fine but the first dump trailer was 5'-8" x 10' with a single 4" cylinder, it would struggle for the first foot or so with a generous load of firewood or gravel. The second one I built I used a 5" cylinder, much better but it was also a 6'-6" x 12' trailer. Both of the Fords got 68" x 9' dumps, the first one had a large (guessing 6" bore) and never struggled, this one I have now I used a 4" cylinder, I suspect it will behave just like the first trailer I built (I haven't tested it with anything heavy yet)
Some good advice about taking more trips with smaller loads, you have to respect it for what it is. Turning up the pressure or upsizing the cylinder will just transfer the weak link to somewhere else.