It's that first inch which matters, I say you must get the film to lay into the innermost spiral. Using the clip helps steer the film towards that first bend so it falls exactly where it needs to. After you get that right, the first couple turns are critical... After that if it feels like it's fighting, it probably is crinkled.

I consider reeling film a "lie detector" kind of activity. If I am nervous and sweaty, I cannot do it and I will have to unreel and reel three or more times. If I am calm and collected, I can do it right every time. Don't let it shake your confidence.