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I too have a driveway that is up hill and looks similar to your incline and I don't have a problem. Based on your pictures, it would appear not be a problem for you.
My tv has a standard bed which is 6.5 ft. The rv dealer wasn't very convincing that I wouldn't have a problem. "Probably " wasn't the advise I was looking for. I was sure I needed to get a slider hitch until I discovered the Sidewinder king pin. Less moving parts than a slider and that appealed to me. I combined with a B&W Companion hitch. I am very happy with this combo. Obviously there are pros and cons to everything. This is another option to consider as you do your research.
Best wishes with your decision.
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