Founded on recent empirical experiences and results from a Housing Adaptation Project accomplished in a Swedish municipality, this paper aims to elucidate and problematize challenges inherent in the process of developing research-based strategies for housing adaptation (HA) evaluations feasible for municipality contexts. In this paper, theory and conceptual definitions of client-level outcomes related to Swedish HA legislation - i.e. accessibility, usability, and activity - are presented. In order to lay the ground for the presentation and discussion on challenges, the Housing Adaptation Project is described with regard to design sampling and data collection, client-level outcomes and assessment instruments used, as well as longitudinal results. The challenges faced during the project were related to the assessment of outcomes, the logistic flow of the data-collection process, client availability for follow-up assessments as well as interpretation of changes in accessibility. Some challenges were due to the organizational HA framework in the municipalities, while others were related to the methodology used for outcomes assessment. Based on our experiences with this project, a set of evaluation recommendations for practice and research is provided.