I've never really thought about this problem, but it occurs to me that one way to deal with it is to look at the difficulty of achieving the end result, which may not be the same as the contest's obvious difficulty.
In the example given, for instance, getting a maid to leave the door open is easy if you can seduce her to your side. But getting her to steal her mistresses jewels - well, the mistress presumably has thought about the possibility of the help running off with her valuables, and there will be a different difficulty there.
Maybe your ability to seduce versus the household's general security, rather than simply the maid's loyalty? It may well be easier this way, not just because you can use your better skills, but the house's strong walls and solid doors aren't a difficulty to the maid, so the full security of the house won't apply to her. But the resistance will be augmented by her loyalty, the risk of losing her join may come into it etc.
In short, I don't think it would be the same stats for the difficulty. But the challenge does end up looking quite unintuitive - Seductive vs. This House is Like Fort Knox isn't a challenge I'd expect, but it might turn up...
-- Jakob Pape "Sometimes subtlety comes in the form of large explosions and jammed open airlock doors."
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