Phylogenetic analyses increasingly take centre-stage in our understanding of the processes shaping patterns of cultural diversity, and cultural evolution over time. Just as biologists explain the origins and maintenance of trait differences among organisms using phylogenetic methods, so anthropologists studying cultural macroevolutionary processes use phylogenetic methods to uncover the history of human populations and the dynamics of culturally transmitted traits. In this paper we revisit concerns with the validity of these methods. Specifically, we use simulations to reveal how properties of the sample (size, missing data), properties of the tree (tree shape), and properties of the traits (rate of change, number of variants, horizontal transmission) might influence the inferences that can be drawn about trait distributions across a given phylogeny, and the power to discern alternative histories. We demonstrate this approach using Western North American Indian dataset societies and show a high rate of Type I and Type II errors contingent on properties of the traits, of the tree shape, and less so of the sample size. While some results may be particular to our simulations, we offer these tools to address some persistent perils in existing cultural macroevolutionary research, and chart outstanding challenges to future work.