This chapter introduces the pilot stage of a Post-Occupancy Evaluation (POE) study undertaken as part of a doctoral research project. The study evaluated the satisfaction and comfort levels of occupants of affordable housing schemes across three development sites in Cardiff, built by the same contractor. The occupants were asked to fill out online questionnaires, to test the user-feedback portion of a complete POE study which is planned to include dwellings’ energy usage, monitored environmental conditions, and as-built construction information. The full extent of gathered data will capture the performance of the dwellings in relation to the occupant behaviour governing energy use within the dwellings. As the first stage of the research, the results presented here give insight into occupant comfort and wellbeing levels of a cross-section of developments, with both social and private households being surveyed. This paper presents the methodology, lessons learned, and next steps for the POE questionnaire. Due to uncertainty and curbs on public engagement because of the Covid19 pandemic, the most valuable learning experience to materialise from the research is the process of data collection itself during stay-at-home measures. The low occupant response to the survey resulting from a distanced approach has meant the focus has been on how to improve and optimise questionnaire design, dissemination techniques, and participant engagement in socially distanced research.