Hi Scott,
Have you considered another zone 'level'? I often have a 'group' zone on one layer (or could be a filter selection) and 'room' zones on another layer (or in a separate filter selection). Its a bit more up front work in model and criteria management, but it provides several benefits, including the scheduling calculations you are looking for.
In your case, the fills would instead be zones, too. They could be called 'workspace' level zones. Then, the larger zone would be the 'group' level zones. The group level zones can respect walls (or not, depending on what determines the group).
I don't work as much with fills, though I sometimes turn on hatching on in my zone settings along with the category color to differentiate one to another of the same 'level'.
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