Older adults residing in rural areas often lack convenient, patient-centered, community-based approaches to facilitate receipt of routine care to manage common chronic conditions. Without adequate access to appropriate disease management resources, the risk of seniors' experiencing acute events related to these common conditions increases substantially. Further, poorly managed chronic conditions are costly and place seniors at increased risk of institutionalization and permanent loss of independence. Novel, telehealth-based approaches to management of common chronic conditions like hypertension may not only improve the health of older adults, but may also lead to substantial cost savings associated with acute care episodes and institutionalization. The aim of this report is to summarize practical considerations related to operations and logistics of a unique community-based telemonitoring pilot study targeting rural seniors who utilize community-based senior centers. This article reviews the technological challenges encountered during the study and proposes solutions relevant to future research and implementation of telehealth in community-based, congregate settings.