Winching - Reverse Auto Tow

Does anyone have particularly bad experiences with pulleys used like this. I am talking about the pulleys themselves. Has someone found a particular diameter that is too small. Obviously larger is better for both bearing speed and rope bending, but there are limitations on cost and availability....particular for the trial run I'm thinking about. I am considering a trial run with a swiveling pulley on the receiver hitch of a pickup, no guides, just the pulley, with around 8,000' of 1/4" poly hollow braid, flying a 1-26. That should prove the launch height, assuming the rope doesn't break on the first launch. I'm not sure what to expect at the pulley end, and don't want the rope jumping out of the sheave, catching and breaking. I doubt it will, but have no experience to back it up.