This pilot study investigated factors influencing the application of connected health (CH) in Taiwanese remote areas. These factors cover issues of cost, infrastructure, technology, business sustainability, business model, collaboration, and communication. It aimed to explore the significance and to assess the feasibility of researching CH in Taiwan. A qualitative exploratory study was conducted by interviewing relevant stakeholders (n = 18). The majority were healthcare providers as most of them are the CH end users. Their feedback was essential in reflecting the effectiveness of CH products and services. Therefore, understanding their views is significant in the design of a successful and user-friendly interactive system. A theoretical framework on the introduction of innovations in healthcare was employed to guide data collection and thematic analysis. Additionally, stakeholders proposed strategies for enhancing the implementation of CH in remote areas. This pilot study also contributed to identifying future directions and information for conducting the multi-stage interviews for collecting the data more effectively. Although the results reveal that the study of CH is meaningful, there is an issue of business sustainability which is obscured by some barriers that need to be addressed. These barriers will be further investigated in the first-stage interview and second-stage interview in future research. The research findings also suggest that strategies and sustainability for CH implementation should be included from the planning phase to benefit all the stakeholders in the CH ecosystem.