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I NEED to be able to back this trailer into my backyard through a 25' wide chainlink gate (gas meter on east side, neighbor's fence on west), and this is coming 90-degrees off of a 25' wide residential alley with fences along both the north and south sides. Bear in mind that this trailer is 26'...

Mount a Pintle Hitch on the front of your truck. You can chase it around better if you see it. Looking at your old trailer with little rust almost makes me want move where they don't salt & calcium chloride the roads. It looks like your driving down a gravel road with a dust plum following you...