[Mtntrek]

Welcome to the forum.

Learning to back a 5w can indeed take some skill and practice. Often it slowly develops as an art form.

Mainly because the pin is directly over the TV rear axle, so there is a delay both in jacking, and chasing the trailer with the tow vehicle. The tail swing on bumper pull hitches gives you more of a head start.

Many inexperienced backers rely on staying neutral to long, once they're jacked adequately. So experiment with chasing the trailer a little sooner.
Plus, there is no shame in taking multiple stabs, or points of a star back and forth. It's all about safety and protecting your equipment.
Keep up the good work, it'll go smoother the more you do it.