I use a winch to move our TC dolley.
First is your winch mounted to a "board." I would switch that out to a piece of flat steel then securely attach the chain to the steel, I would use all steel for the winch assembly. Our winch is attached to the 6" concrete floor with a grade 8, 5/8" steel bolt 10 inches long, its a jam fit and its not coming out with any side pressure on the bolt.
As far as whether the winch is able to be reused, unless it is physically damaged, that is burned up or the gears are stripped it can be unwound and start over.
I use 3/16 inch steel cable and keep it from kinking too badly by going slow and sometimes, with the winch stopped I will grab the cable, wearing gloves and manhandle it into position. It works surprising well and has for 5 years.
You may just need to start over with a new cable and be careful with it and don't let it kink. My cable wants to lay flat on the winch drum and when that wrap of the drum is full, start the next warp and that is where there can be trouble, just go slow and make the cable do what it needs to do and you will be okay.
You will have the same problem you now have with the new miracle ropes. They will bunch up as well. Some boat winches use a flat strap, that will work but abrasion is an issue.
Good luck.
