From my point of view Rumple wouldn’t saddle Regina with that curse unless he wanted her dead or dark. Rumple is not the sort of man who would punish Regina just for spite there has to be an ulterior motive for that particular consequence of the curse. I just can’t shake the sense that Regina’s part to play is more significant than everyone with the likely exception of Rumple knows.
The consequence of the hole could be that Rumple knew that Emma’s child would lead the Savior to SB and that child would also be Regina’s adopted son. The ONE thing Rumple didn’t count on was that Henry would be Bae’s. That never even occurred to him and he didn’t see that.
I have to agree with RG on this I believe Rumple had forseen that the Savior would have a child and the child would bring Emma to SB to break Regina’s curse and that Regina would adopt the child & that she would come to him for help to make that happen. But I have feeling that adoption wasn’t legal and that is something we will find out in the episode. I don’t think Rumple counted on Emma & Neal(Bae) meeting, falling in love and producing Henry who we know now is the truest believer.
Keeper of Neal/BaelFire's Blood Magic, Neverland Crossbow, FTL Clothes,Room at Granny’s, Charming & Emma’s Father/Daughter Hugs, Henry's Neverland Crossbow, Rumplestlitskin/Mr.Gold's FTL Walking Stick