Her plan was to voluntarily retire in 1993 or 1994, IIRC. By then Portillo might have a chance at succeeding her, particularly if he gets promoted to a Great Office after a 1991 or 1992 election victory. The leadership contest would probably involve him, Major and Heseltine.
Huh, that's interesting, I didn't know that.
Tbh I doubt there's much of an opening for Portillo in 1993-1994. The opening was created due to divisions over Maastricht, but with Thatcher that goes out the window, and I don't see the 1990s Conservative Party electing a 40 year old as their leader without a desperate situation. Plus, I think there's a chance that his personal history comes out earlier in this scenario if he runs (which I suspect is part of the reason he didn't challenge Major IRL in 1995). I suspect Major still ends up becoming PM in this scenario, but a few years later, and then still loses in 1996-1997.
I'm not sure why she so desperately wanted to stay in office just to retire 2 years later, given how long she had already been there. Also, she was NOT winning in 1991-1992. The country had tired of her by that point. Pretty much everyone except for her could see that.