Loading a plastic reel is easier to begin with... But as WayneStevenson says, the important thing with stainless steel reels is to get the film started square and centered on the reels. I don't know exactly but I imagine you have 1/16th inch tolerance on the centered-ness. By feel, as I start the film under the clip, I feel left and right to make sure it's equal.
After that, I listen for crinkling and of course if the film finishes dimpled or if the film runs out before the spirals run out (35mm/36 exp should finish on the last spiral). If there is a winding error - there is no option. Unwind all the way to the core and start over more carefully.
On a good day the film always goes on right the first time. On a bad day I have to unreel and re-reel three times. With gloves on and careful handling, there is no harm done. But there is risk of fingerprints if you do it bare handed.
Good luck, you can choose plastic if you want. You've gotten some good advice (dry reels load easier because water will cause film to bind).