Could I use a jack caster wheel to solve this problem?

Airbags do sound like the easy up easy down solution in your case, but think about airing them back up when you get back home and are backing in.
Long enough air hose from your compressor, or pirchase a decent 12V compressor, air tank, or integrated airbag system with compressor.

Bobbo wrote:
Weight Distribution Hitch. Transfers some of the weight that is resting on the tow vehicle's rear axle to the tow vehicle's front axle (to maintain steering) and to the trailer's axle(s). May, or may not, include sway control built in.

Thanks for the definition and yes, I have a wdh.

Weight Distribution Hitch. Transfers some of the weight that is resting on the tow vehicle's rear axle to the tow vehicle's front axle (to maintain steering) and to the trailer's axle(s). May, or may not, include sway control built in.

bartlettj wrote:
Are you using a wdh? It sounds like you need one.

What is a wdh?

Are you using a wdh? It sounds like you need one.

Grit dog wrote:
BTW, how much c rap are you putting in the back of the truck after you have the camper loaded?

My wife does like the comforts of home, but it’s my scuba diving equipment that takes up all the weight. Just the scuba cylinders when full of air add up to almost 200 pounds. Not to mention the tandem kayak on the cap.

Using a ball with a 5 inch riser worked but in the end I found it stressful to change the ball in the middle of the street. As for the boards, I have an angle to take into account; I’m not good enough to backup directly on the boards in these conditions. So the best solution is to have Air bags installed on my truck and this will solve the problem.

Thank you all for your great advice.

I'll say not enough info to advise. I understand basically what is happening, but the why could be many reasons.
If everything is fine and to your liking when loaded up and headed down the road and the problem really is just a really bad dip or break over angle in your driveway that is worse than to be expected anywhere else, then some boards, airbags, higher hitch, etc should be the answer.

BTW, how much c rap are you putting in the back of the truck after you have the camper loaded?
Are you one of those, Traeger, 4 bikes, load of firewood, 5k generator, pop up tent, swingset for the kids, 200qt cooler with 3 racks of 'Stones on ice and a dog crate for your wolfhound kind of guy?

I’d just use a couple 2x6’s under the truck tires to give you the clearance you need, cut to length you need the extra height. Stack a couple if 1 not enough.

You won't bend the frame on the trailer. You'll just bend the jack and break the caster wheel, almost immediately.

Trailer jacks are really only meant to hold the trailer tongue up. They are not designed for side loads imposed on them by pushing the trailer around, let alone being towed with the weight of the truck also on the jack.

Commercially available trailer jack casters are just cheap plastic wheels with stamped steel frames. No bearings. They won't roll unless the trailer is EXTREMELY light on the tongue.

Speaking from experience here. The only trailer I was able to use a caster on effectively is my single-axle 6x10, and then only when it's empty.