You hold the film on the edges and let it slip through while winding it on the reel. There’s a bunch of videos that show the process. It’s pretty straight forward.
As with everything: pratice first until you can literally do it blindly.
I don’t wear any gloves. I start with clean hands and whatever tiny fingerprint-fragment might get onto anything, will be dissolved multiple times by the chemicals anyway :-)
Plastic reels just have a tendency to jam. In the end it’s basic physics. You push a thin and flexible material down into a spiral. At some point the resistance will win.
If you keep your plastic reels clean and dry(!) and use films with a decently thick base, it usually still works fine though. Once you use a a film with a more flimsy base, this will turn into a problem.
The make of the film material is basically zero problem with metal reels though, because you wind the film onto them. No pushing of flexible material involved. Metal reels also just work fine if you get sweaty hands inside your changing bag because it’s summer and everything is hot.
I mostly use metal reels nowadays. Because the handling is absolutely predicatable and they’re also easier to clean and dry. Sometimes i still use the plastic reels, because i have them, but only with films like Ilford. Because they are thick enough to not jam up everything.
Because of Windows.