Hi Taz . I am glad that you bring thus up again. There are many users frustrated with the "Smart Assertion" feature (me included).
See an old post here : https://community.smartbear.com/t5/ReadyAPI-Questions/Issues-and-Feedback-about-Smart-Assertions/m-p/228752#M55442
Bottom line: The current "Smart Assertions" feature does not accommodate the majority of the ReadyAPI user's needs and I for one am eagerly awaiting a SmartBear ReadyAPI update on this...
No easy way to assert unordered results. Currently only complex scripting does my trick. Or, if you don't mind some loss in coverage, the assertion groups can also help ("assertion 1 OR assertion 2" see https://support.smartbear.com/readyapi/docs/testing/assertions/index.html#assertion-group)