As indicated in the question if I use any combination of Filter or Space WITHOUT a board in the "work in your plan" then even if I have the setting under "Estimation and Scheduling" - "Work items with empty start or end date fields" set to "Use dates from their assigned sprint" the roll-up dates don't work and they're just blank. They'll only roll-up hardcoded dates from the Start date/Due date fields. I don't want to hardcode dates though. I want the dates to reflect the reality of changing work on the team... ie having the roll-up dates reflect the sprint dates the work is actually happening in.
This doesn't work though if a board isn't included. Yes I can hear the first question already of "why don't you just include a board?" and the reason is my Plan is for a specific cross functional program and the teams work on multiple programs at a time. I don't want to reflect everything that everyone is doing in a plan specific to a certain program.
