Coordinating requirements engineering (RE) and evaluation studies across heterogeneous technology-enhanced learning (TEL) environments is deemed challenging, because each of them is situated in a specific organizational, technical and socio-cultural context. We have dealt with such challenges in the project of ROLE (http://www.role-project.eu/) in which five test-beds are involved in deploying and evaluating Personal Learning Environments (PLEs). They include Higher Education Institutions (HEIs) and global enterprises in and beyond Europe, representing a range of values and assumptions. While the diversity provides fertile grounds for validating our research ideas, it poses many challenges for conducting comparison studies. In the paper, we first provide an overview of the ROLE project, focusing on its missions and aims. Next we present a Web2.0-inspired RE approach called Social Requirements Engineering (SRE). Then we depict our initial attempts to evaluate the ROLE framework and report some preliminary findings. One major outcome is that the technology adoption process must work on the basis of existing LMS, extending them with the ROLE functionality rather than embracing LMS functionality in ROLE.