I really want to believe that Rumple is trying all options to get to our world before he resorts to using the Dark Curse. He’s training Regina to make her a monster in case everything else fails, but he wants to try all options first. The Curse is a good option, but it does mean waiting for Regina to come to full power, waiting for Snow and Charming to fall in love, making sure Charming and Snow get pregnant, and then waiting an additional 28 years until Emma shows up to break the curse. These things Jefferson is getting for him could speed up the process, help him get to our land, get Bae, and get back without having to do all this pesky waiting.
As to those slippers: unless the magic of the slippers is that they take you to Kansas, no matter where your home really is? The writers could get around “no place like home” like that.