i have not been crewing very long so if this post sounds dumb thats the reason.
with this kind of wrap you also loose line gained when you let go of the loop.
would this describe how you put on a tarditional wrap with the winch loaded? right handed trimmer: left hand holds the tag end or bitter end of line slightly above the winch following the right hand making the wrap. i dont see how you can get your fingers caught since your holding the loose end.