For me, this whole thing goes in the category of "what the @#$ were they thinking?"

I'm not sure if I should interpret it as a isolated case of misjudgment, evidence of poor organizational features, overinterpreting the significance of this by outsiders (the Iowa caucuses are notoriously fuzzy, which is kinda the point of them, so maybe the party saw this as an appropriate test case?), technological naivete, or what.