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What am I doing wrong here?
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This is IMHO only, as you will probably have your trailer on the road before I have mine.
I suggest that it's the next step you need to look at, The trailer box 50% outside The Template in both the top and plan view. You could put a little template on the trailer box.
Personally, I like this one. You could take a size-graduated set of inner tubes, string they on a bungee between the trailer and car and then inflate them. Match the body color with Plastidip S.
Or make it like a bouncy castle.
It would like like a caterpillar or the larval stage of a flying car.