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Math and physics of backing in a trailer with a pickup truck

Our tow ball is the same as seen in the photo. Our trailer is similar as you see in the other photo. The blue arrow to the bottom of the jack and the red arrow to the left side of the tongue of the trailer. When backing the truck into our driveway we could turn the wheels of the truck to the left or right as needed to maneuver the trailer into place. If we were too sharp on the left side then the truck bumper would approach the side of the tongue as seen by the red arrow. There is a dip between the asphalt road and the concrete driveway. When backing and the trailer jack was raised as far as it could be raised it still nearly touched the bottom of the dip (concrete).. The tongue is heavy and exerted weight on the truck bumper. It did not scraped the dip but it came close. Now we need to empty the trailer and back it into another driveway. This one is different in that the driveway is on an incline starting near the top of the asphalt driveway. There is no curb so it is smooth from the road to the end of the asphalt driveway. About 25% of the driveway is asphalt and the rest compressed dirt and gravel. The tow ball and tongue are made to swivel with movement of the truck to make left and right hand turns. As we found out when backing in the current driveway the ball had some movement when the dip was encountered. The new possible problem is that the truck will be on the road while the trailer will be on driveway which is an incline down. With my car I got a rough estimate that maybe the angle as seen in the third photo was around 30 degrees. 


How large an angle before the backup of the trailer and truck gets to a point where the inclined surface prevails?


This driveway is near a curve in the road. Backing up a trailer is somewhat of a skill and I got this one backed in at the current location on the 2nd try. With traffic in both directions and the truck in the road I can only hope that I can get the trailer where it needs to be in 1-3 tries. Horns may sound, people may yell idiot, etc. I'll choose what I believe would be the time with the least traffic on the road which will likely be Sunday morning.


The tow ball is made to allow movement left and right by the truck. From the current location I found out that a dip can cause the jack to drag. This new location will also involve a left hand movement of the trailer tongue. But the new and never experienced movement will now be the truck at a higher elevation the the trailer. I'm not clear on how it will affect the entire project of backing the trailer into a spot that is lower level than the road. 

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Two crude images. I've experienced the dip and got it done.
Now the incline must be done. Worst case have to sell the trailer.
The ball will allow movement down for the tongue but how many degrees not sure.

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What about a hitch with a rise?  Keep the regular hitch for travel and pop a raised or lowered hitch on for these odd spots.

That looks like a big trailer for that truck.
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Scott:
The trailer is 18 feet. Here is the type tow ball we have. Mounted on the bumper.
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I'm going to try to get a ground level view such that the more precise angle can be determined. I'll measure all 4 un-equal sides as well.
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I'm not finding clear definitions of baulks and cribbing. I'm in the USA.

My truck has had trouble moving on wet or inclined surfaces. The way this driveway is located, I backed in today (no rain or anything) and with the incline up I had to get up some speed. Near the streets edge here comes a car around the curve. I had to stop with my truck stationary on an asphalt surface. I would have to have an empty trailer and somehow get it in the right place and perpendicular to the road. And likely need to create a concrete or paver pads for the wheels of the trailer to rest vs. resting on soft damp grass.
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Baulk of timber is a roughly square wooden beam, cribbing is a stabiliser pad or temporary construction timber.
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andy
Please explain how those would be used. Thanks.
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The house where the trailer would have been parked was not bought. We were planning ahead to know if there was room to store the trailer. There is but the purchase was abandoned for other reasons.