I'll be honest with you. I've towed many a trailer in my time and currently own a 24' enclosed cargo trailer I use quite a bit. I also tow a lot for work. Anything from small compressors to the largest track skid steers made and most recently a 900 CFM compressor that is giant.Well, the in laws trailer is out, so that solved that quandary.
Now I just wish that I could borrow someone's trailer for a day to practice parking it.
That's my biggest worry right now. Having to back it up. And unfortunately, the rv spot I have booked isn't a pull through spot.
I have found that the longer the trailer and many times the heavier the trailer the easier it is to back up. Short trailers like single axle utility trailers for towing atv's, mowers etc, are shorter and can get get jack knifed very quickly and take a lot more and faster steering wheel corrections to back up properly. Longer trailers, especially tandem axle trailers require less steering wheel input and are much slower to jack knife allowing you time to correct without having to keep pulling forward to correct your backing mistake.
In the end, when backing have a reliable spotter standing in view of your drivers side mirrow and each of you on your speaker phone so you can communicate without yelling to each other. If you are still unsure of your clearance whilt backing up, GET OUT AND LOOK to verify your distances and space. I alos find it easier that if you are backing in an arch to have that inside arch on your drivers side meaning you are backing up in an arch going to the left.