Understanding the real-world end-to-end performance of residential Wi-Fi and broadband networks is essential for consumers, service providers, and policy makers in an increasingly connected society to determine how connectivity can be improved, through better technology or appropriate spectrum decisions. While previous research has studied such performance, the focus has primarily been on the wired Internet, pointing to Wi-Fi as a bottleneck without investigating the reasons thereof. We believe that the preliminary results presented in this paper, from in-depth studies of residential Wi-Fi deployments in a small Midwestern town, offer a first look into how the Wi-Fi environment may impact the user experience. Over a period of six months, we deployed single-board computers to measure the throughput and latency of Wi-Fi and the backhaul broadband network in a number of different residential environments, as well as capture the Wi-Fi signal environment. Our analyses show: (i) interoperability issues between AP and client supporting different Wi-Fi amendments (e.g., 802.11ac, 802.11ax); (ii) a lack of smart interference management and Dynamic Frequency Selection (DFS) support, resulting in over-usage of channels in the U-NII-1 and U-NII-3 bands when other, less congested bands may be available.