[...]
Holydarkness should chime in and send this thread to his contacts. Maybe I’ll get an actual reply from Roobet—or at least from him—about their final answer. This isn’t just for my clarification, but for everyone else to understand why the casino let this screw-up happen. I want an answer as to why it happened and what they’re going to do about it.[...]
Holydarkness what?
I believe that "should" in your sentence refers to a polite request, like "I will appreciate holydarkness's insight and attempt to reach Roobet" instead of a demand like, "holydarkness have to reach Roobet to address my issue"?