Wheels on rear

Is there any way you can lessen the slope of the drive at the bottom so as to reduce the initial angle of attack? Perhaps some asphalt so that the back wheels of the trailer begin the climb BEFORE the stabilizers hit. Just a thought!
This suggestion can often solve this issue. A wedge of asphalt that starts raising your trailer earlier at the edge of your driveway may give you enough clearance. If this is a legal issue, 1 2X8 and then 2 2x8s nailed together could create a temporary ramp to the edge of your driveway. It's a geometry problem.
 
I'm with the majority on no tadding wheels.
be careful of adding wheels to the reciever hitch, it is designed for whanging weight, not pushing upward. Liek said previously, yo umay be asking for trouble or damage to the rear wall(s) of the trailer.
My thought, figure out a way to change stabilizers closer to the rear axle, then build a toung jack and have it welded to a 2 inch square tube that fits inside the receiver and use it to help stabize as needed. I will try to add a picture of a couple friends have. I will see them tomorrow.
 

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