To be clear, I'm not talking about pigtail vs. no pigtail. I'm talking about the position of the rope guy relative to the device. If you are standing straight to the side of a fixed bollard, so that the rope doesn't bend around the fairlead before going onto the drum, then it can jump over itself and cause problems. The rope has to take a good bend at the fairlead to go true onto the drum. None of this is an issue with a porta-wrap style device, because they self-align to the rope, it's only an issue with fixed bollards.
The definition of a rope fairlead, as I understand it, is something that takes an incoming line from an unfavorable angle, and changes it to a more favorable angle. So even though you may have the rope through the pigtail, it's not operating as a fairlead at all unless it's changing the direction of the line. And it's that change of direction right at the bollard that keeps the wraps running true.