If a user selects a checklist on the Create File screen, then any events that are based upon the closing date will not appear because the actual closing date cannot be entered until a user gets to the Financial screen. If a closing date is then entered on the financial screen, any events based upon closing date will never populate until the user goes to Misceelaneous Change and deselects the checklist and then reselects it. This is not really a request for a new feature, but more for a fix of an existing glitch. Perhaps if the closing date on the create file screen was not the projected closing date which seems to have no functionality within the file, this might be fixed.
And if the closing date changes, the timeline of the checklist should automatically update with revised closing date!