Bi-directional relationship not function as expected.

I think I understand what you are trying to do, and I think there is a solution.

Have you tried creating a small, 2 column table, where you have the OrderID and calculate the Earliest Work Record Date based on the OrderID from the Work Records?  Then, you could Left Join that small table to the Order Facts table, and thus get your Earliest Work Record date into your Orders Fact Table.