At times both of these are AI generated field. Sometimes I want to list the Page Name first on the main list and the Sheet # second. What controls which is first? Is it a toggle?

Hey Jeremiah! Right now, the pages always display as "(Sheet #) - (Page Name)". If there is no Sheet #, then it's displayed as "(Page Name)". We don't have a way to control the order of how this is displayed yet, but I'll forward this to the team to see if we can add this as a user setting.
you could manually change it, you can highlight on the plan what you want the page to be called, then choose page name all, do it again for the sheet number and select all choose sheet # all.