This is super helpful — thank you. Here's how I think they can be solved:

1. Flagging special events by pulling from the booking system so the schedule doesn’t assume a “normal” Monday.

2. Tagging staff by skillset (large parties, wine, expo, etc.) so the optimizer doesn’t just fill slots but matches people to the right shifts.

3. Flexible availability instead of binary availability — things like “prefer not,” “can pick up if needed,” “no doubles,” “no clopens,” or “I already have a cover lined up.”

4. Transparent fairness — showing why someone got (or didn’t get) a shift, how hours were distributed, and what trade-offs were made so it’s not a black box.

5. Built-in shift-swap handling, since FOH often sorts coverage themselves before the manager ever touches it.