The evaluation of investments in advanced technology is one of the most important decision making tasks. The importance is even more pronounced considering the huge budget concerning the strategic, economic and analytic justification in order to shorten design and development time. Choosing the most appropriate technology requires an accurate and reliable system that can lead the decision makers to obtain such a complicated task. Currently, several Information and Communication Technologies (ICTs) manufacturers that design global products are seeking local firms to act as their sales and services representatives (called distributors) to the end user. At the same time, the end user or customer is also searching for the best possible deal for their investment in ICT's projects. Therefore, the objective of this research is to present a holistic decision support system to assist the decision maker in Small and Medium Enterprises (SMEs) - working either as individual decision makers or in a group - in the evaluation of the investment to become an ICT's distributor or an ICT's end user. The model is composed of the Delphi/MAH (Maximising Agreement Heuristic) Analysis, a well-known quantitative method in Group Support System (GSS), which is applied to gather the average ranking data from amongst Decision Makers (DMs). After that the Analytic Network Process (ANP) analysis is brought in to analyse holistically: it performs quantitative and qualitative analysis simultaneously. The illustrative data are obtained from industrial entrepreneurs by using the Group Support System (GSS) laboratory facilities at Lappeenranta University of Technology, Finland and in Thailand. The result of the research, which is currently implemented in Thailand, can provide benefits to the industry in the evaluation of becoming an ICT's distributor or an ICT's end user, particularly in the assessment of the Enterprise Resource Planning (ERP) programme. After the model is put to test with an in-depth collaboration with industrial entrepreneurs in Finland and Thailand, the sensitivity analysis is also performed to validate the robustness of the model. The contribution of this research is in developing a new approach and the Delphi/MAH software to obtain an analysis of the value of becoming an ERP distributor or end user that is flexible and applicable to entrepreneurs, who are looking for the most appropriate investment to become an ERP distributor or end user. The main advantage of this research over others is that the model can deliver the value of becoming an ERP distributor or end user in a single number which makes it easier for DMs to choose the most appropriate ERP vendor. The associated advantage is that the model can include qualitative data as well as quantitative data, as the results from using quantitative data alone can be misleading and inadequate. There is a need to utilise quantitative and qualitative analysis together, as can be seen from the case studies.