Among the available solutions for building heating and cooling, district heating (DH) and district cooling (DC) systems are considered some of the best options since they can ensure a better control of pollutant emissions and greater efficiency than individual systems. Nevertheless, improvements are needed to increase their sustainability and reliability. The so-called “low temperature district heating” (LTDH) concept has been introduced in recent years in an attempt (i) to reduce the distribution heat losses through a temperature decrease in the DH network, (ii) to favor the integration with renewable energy sources, and (iii) to create the conditions required for the development of future smart energy systems. However, many concerns have been raised about its implementation in both existing and new systems. For this reason, this paper aims to identify the stakeholders’ ranking of the barriers against LTDH system development and implementation over the next few years. Aiming to this, a questionnaire was designed, including an analysis of current gaps and strengths, and then submitted to more than 50 Italian and international experts in the field of DH. An in-depth analysis of the received answers was performed, focusing in particular on the Italian experts’ answers. Comments and suggestions on how to promote the transition to the new LTDH approach are reported.