A nice little hack to fullfil the limitation of the Chalice's second option is targeting a low sanity investigator and equipping St. Hubert's Key; it helps keep the Key in play while also being able to get rid of the doom easily. An investigator that can take those cards and benefit from the synergy is... "Ashcan" Pete! What's more, with his ability it's also possible to use the first option of Hallowed Chalice twice in rounds the agenda would advance anyway.
Not an insane combo, but you might get more out of this card than you think.