The paper offers an experience-based viewpoint on two key phases of the development of an Information and Communication Technologies (ICTs)-based system: the definition of requirements and identification of related criteria and methodology for its evaluation. In doing so, it refers to the unique context of the i-Treasures EU project, which deals with the development of an innovative integrated platform to support the learning and transmission of Intangible Cultural Heritage (ICH). The i-Treasures integrated platform is conceived to support both traditional learning approaches and innovative and active learning processes, based on extensive use of sensor-technologies. In this light, during the development process, particular attention has been devoted to the definition of requirements with specific reference to sensor-mediated Human Computer Interaction (HCI) issues and the evaluation process was designed accordingly, in coherence with the specific advanced features of the integrated platform. The paper offers a view of the complexity of the design of ICT-based tools supporting the preservation and transmission of ICH and also provides an insight (and this could have a broader impact) into the methodology adopted to harmonize the requirements and the evaluation phases which are key pillars for the construction of any educationally effective ICT-based learning system.