I believe I found the trigger that was misfiring causing me to be unable to get Odette's new Halloween content.
If you have already completed Eve's route, and you've had sex with Grace, you can use a couple of console commands to hit the triggers in the code that weren't working correctly.
Enter these commands:
Machine.trigger(T_ode00_init, from_load=M_odette, force_save=True)
Machine.trigger(T_all_sleep, from_load=M_odette, force_save=True)
The next weekday morning you enter the tattoo parlor, you should get the first Halloween scene setting up the new content.