I completely agree with your two main points. That the blackmailer hasn't really tried to hurt Ashe so far, and that Delilah is helping them. I'm not convinced that Ms. X and the blackmailer are the same person. They could be, but the evidence seems to equally point to a new player. As you point out, most of the blackmailer tasks have been rather benign for a blackmailer. Secretly drugging a party with a crazy new street aphrodisiac is a big step up in potential harm and chaos. Doesn't feel the same.
If Delilah is helping the blackmailer, I want to know how? Did they recruit her, or blackmail her into service? If she loves Ashe, what kind of blackmail would work on the romantic and idealistic Delilah? If they recruited her, who can gain her trust, or convince Delilah that this will help Ashe? I can't think of a perfect fit, but if I slap a little tinfoil around it, Delilah's other mom, Victoria, could fit.