@upcountry, I know EXACTLY what you are talking about. You know what you are doing but you say to yourself, "its ok this one time" or "I'll take care of that later". That is when you get bit.
I will say, if you have steel cable, now would be a GREAT time to upgrade to synthetic. Mine has been massively forgiving and a lot easier to work with. I know its ~$300 you weren't planning on spending, but its worth it.
As for winding in the cable, I always did it in a parking lot, strapped to a big concrete pillar at one end (BTW, old decommissioned tow straps work GREAT for attaching to such an object). With the truck in neutral and off (you can have it on, whatever) and the winch cable all the way out, begin winding in. With my hand ~5 feet away from the fairlead, I guide the rope in. The tension of the truck tugging on the rope keeps everything nice and taught. If the rope starts crossing up or not all nice and pretty, I stop, back off, and do it again. Also as I'm doing this, I often turn the wheel a little bit as needed to correct and keep me fairly straight.
That would be my recommendations. Also FYI, I recommend continuing using gloves with synthetic rope. Rope burn is rough and sometimes surprises get stuck to the outside of the rope...think thorns! OUCH!