Should I replace this winch line? ….hawse cause this?

Driveway is about 150' (so 100' of line means about a 7-8 foot rise as the truck is pulled up the hill)
I've done it alone before, but normally I suggest have someone in the driver seat just to stab the brake if something goes wrong while doing it.

The way I do it is walking alongside / in front of the truck as needed as it's spooling in. When the cable gets to one end of the drum, I'll steer the vehicle the opposite way so as to encourage the rope to start winding toward the other end of the drum.

There's a method to it for sure... But after having done it dozens of times, it's become almost second nature. Coordinating everything becomes easier the more times you do it.

 

That’s similar to what I did the first time.
I didn’t feel comfortable doing it all outside with no one behind the wheel!

 

When I put my new line on, I installed it on the drum, Attached my Tree Saver Strap and Winch Rope to my Kioti Tractor and had the Truck pointed in a straight line, I had the Truck Running and in Neutral, I walked in front of the Truck spooling the line on. It was a slight slope to the tractor.

 

I did similar but not outside when pulling and to a large transmission tower footing.
Next time I’ll find more of a slope.