I have thought about evaluating the Boolean data in TestStand but, as you say, this is a lot of work. What I have been doing is to map the boolean data to integers in LV (very easy) and then use the multiple numeric step type to evaluate the integer array automatically. This feels kludgy and I have tried a couple of times to create a "multiple boolean" step type with little success. I'm surprised TS hasn't anticipated a test returning multiple pass/fail results. I do this all the time for production code.
What I have tried is to copy MultipleNumericLimitsTest data type to a custom type and add a BooleanArray with a data type Array of Boolean[0..empty]. Then when I specify module, I select Step.BooleanArray as the value. The last step (that I know of) is to select Step.BooleanArray as the data source in the edit limits window. At this point if I run the test, I get the error "expect numeric, found boolean" (or something similar). When I look at the properties of my custom step type, the Substeps has DoMultiNumericMeasEvaluation as the Post-Step. I believe this is the root of my problem but I can't figure out how to change this to "DoMultiBooleanMeasEvaluation" or similar. Any Ideas?