Hmmm... This might require some code investigation.
I did find a couple of problems with the definition of getting the spy watch not triggering properly. I've patched these up now but it may be a little until the patch hits. For the mean time, if you get Haily's package corruption, it "should" fix this.
As for Cassidy whisking you away when you attempt to use your hypnosis powers for sexual stuff... That's how Cassidy rolls... However, for Jenny's hypnosis content, putting in the effort to make sure she is properly hypnotised instead of just faking it will result in significantly less blowjobs.