Lucidstuck I

If this plan does not go smoothly, it will be obvious that the Observers are involved, since it is too complex for someone without near-omniscience to accomplish and Daydream doesn't quite have the ability to interact that we do. If something tips off Lucia that Alice was involved - perhaps, after the mission is over, and someone mentions it? Or even Alice herself showing back up and mentioning it because she can be a little vindictive and bitchy that way? Then having had it happen behind her back without a chance to come to terms with the idea that it was happening can easily make Lucia more suspicious of our commands or even invoke her ire in our direction.

I stand by the 2. option as it is, with the hopes that we're allowed to guide conversation upon arrival.
That said I do not oppose the Discord order-chain, just pointing out a larger unknown factor and more points where it can all come tumbling down. I advise caution, as always.