I have always been too scared to put my transfer into anything other than "neutral" for winching - because I know my rope needs to be kept taut in order to get wound onto my drum neatly/properly.
Loose rope + inward-winding-winchdrum = jam-ups, tangles, damaged rope, and worse (ie - breakages).
(And even winching with the rope kept taut - I still succeed in getting things "messed up" occasionally - Usually when the situation forces me to choose an anchor point that's off to one side where the rope builds up on itself (on that same side) rather than being wound evenly across the whole width of the drum.)
PS. --- But it sure looks cool when I see people spinning their wheels while winching. (However it's just another pleasure I can't afford.
)