I wouldn’t worry about it too much Rich. I appreciate the neat and tidy approach, but if you spool it like a garden hose or maybe a cable drum (in your instance) it can pull in under tension and it can be a bugger to dig / pull the line out again.
The dyneema tends to flatten as it spools IME so maybe less jamming than with a cable.
If you find you can’t rig it to pull straight, then keep a close eye on it as it bunches at one end, you know I’ve just busted mine by being careless, and I’m not on my own doing this.
In a way, the fairlead not going to the extreme would / should assist it feeding better if your winching at a n angle, at least there’s somewhere each side of the static feed point then.
Just my thoughts having done a bit of it. One thing, when you’re stuck and need the winch when alone, you’ve usually spent 1/2 hr or so trying other things, you may be on a 1:3 slope, heaving open the door a dozen times again gravity, your slipping and sliding on mud laden boots and getting knackered... that’s when you (me, I) tend to make mistakes, so the neat-and-tidy aspect tends to go to the bottom of the to-do list.
You’ll have to run it all off again to wash up properly when you get home, so that’s when OCD can be allowed to kick in
Don’t be lazy and leave it full of mud, but who am I to tell you that mate, I’ve never seen you in the slightest be untidy