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Upgrading Milestones PM Unmanaged - Assertion Failed

I am running into what seems like a common problem with Milestones.  Someone installed the unmanaged version of PM+ 1.53 a while back and when I was trying to upload new code to the system, tests for milestones failed - preventing me from doing anything.  I decided the best route to take was to upgrade PM+, using the Eclipse IDE.  I have had to make a bunch of changes to the test code for the system.  I am turning off all the validation fields and workflows when trying to deploy the code, and am now down to one error:

"System.AssertException: Assertion Failed"..."Class.Milestone1_Test_Field_Values.testFieldValues: Line 372...".  I'm at a loss, I've checked what I think is every dependency and whatnot ...

 

Any advice you can give me? It would be much appreciated.