The process of heritage interpretation through the digital simulation method has been tested as an environment required for the process of restoration, conservation and design for the future of a heritage site. However, this paper questions whether the digitally collected data and heritage interpretation/ representations which are a useful tool for professionals like architects and developers lead to critical evaluation, inspiration and engagement for the heritage owner/layman. The former Portuguese colony of Diu Island, UT, India, presents an array of tangible and intangible heritage featuring a Portuguese fortification and churches along with the historic urban fabric of Diu Town as a complex and historically relevant primary case study. The various methods of heritage data capture and the opportunities the outputs create for interpretation/representation will be evaluated in this paper. The methods of capturing data to interpret heritage values covered in the paper are traditional building survey, laser scanning, photospheres and photogrammetry. The discussion begins with inherent advantage and disadvantages within each method of heritage data capture, ways in which the heritage owner and the local community can be active participants in the data-collection process and, most importantly, the output of the datacollecting techniques. This leads on to the core of the paper which questions the output of the collected data and its wider opportunities for representation of the values of heritage to heritage owners/layman. The paper evaluates the outputs of the digitally/non-digitally collected data to understand the opportunities of heritage representation that can allow for layman engagement and inspiration towards heritage interpretation and conservation in a part of the world where such practices have not been common in the past. Furthermore to gain professional advise on structural and design work to adapt or conserve the heritage structure.