Hi Chance, are you applying the oil to a hot pan or a cold one?
The way I do it, learned right here, is to heat the pan in stages to 500 degrees. Pull it from the oven and apply your oil of choice, I use crisco. I wear a thick pair of leather gloves, but still handle the hot pan with a folded kitchen towel. Before it goes back in the oven, wipe it off with paper towels best you can. It should look shiny, but not wet. Bake again for an hour and repeat. I do at least 3 coats, sometimes 4. This has produced very black shiny skillets for me.
What did you use to get the rust off?