When I was 15 and just started driving, my dad put me in his crew cab F350 standard transmission diesel and had me hook up to his 16 ft flatbed car hauler that I could barely even see from the drivers seat. He told me to back it into the gate from the road, down towards our barn and line it up to my moms car as if we would be loading the car onto the trailer. It was probably a good 400 feet from the road to the car. He told me I wasn't getting out of the truck until I learned how to back up a trailer. It probably took me 3 hours and I'm not sure how his clutch survived that ordeal, but I figured it out, albeit with a pretty sore left leg from all that clutching.
I find that the longer a trailer is, the easier it is to back up. I do better going uphill with a 24 ft stock trailer than flat ground with a 12 ft dump or flat trailer. In any case, it's nothing more than practice required before you can get to where it's almost second nature. Taking it as slow as possible with very slight corrections is the key. Having good tow mirrors and watching the trailer without having to turn your head around is helpful as well.
If you ever want to feel better about your skills, go sit at a boat ramp and bring some popcorn. I swear half the people I see at a boat ramp must have never been in a truck before, much less backed up a trailer.
Now I wish I'd have realized what we had in those particular cows and I wish my dad and I had gotten along better so we'd still have the progeny from them.
