Nowadays we face the increasing significance of regions as social, cultural, political and economic interaction systems (Agnew, 2000, 2001 and Haukkala et al., 1999 in Palekiene, Simanaviciene, & Bruneckiene, 2015). Due to the ongoing changes in global economy they face several challenges regarding the well-being of their inhabitants. Meanwhile, it is worth to consider that the different inhabitants and stakeholders would have different preferences for the development and use of various sources of the settlement. The differences in the utility functions may lead to conflicts. These conflict would arise among new comers and current land owners, businesses and NGOs or among inhabitants too, even among generation groups (like the case of "OK, Boomer"). As the economic concentrations attract increasing number of residents small and medium-sized towns (SMSTs) must design programs which improves their population retention. Challenging that, the KRAFT ('Creative City, Sustainable Region') Concept developed by iASK (Institute of Advanced Studies Kőszeg, Hungary) is a regional development initiative, which focuses on the connectivity and cooperation of key players. One of the major outcomes of the initiative is the 'KRAFT' complex system of indicators ('KRAFT-index'), an analytical tool suitable to demonstrate regional development tendencies regarding eight specific development areas (economic development, governance, social vitality, health, culture, networks, natural and built environment and education, learning). In 2017 we have conducted an on-site survey: during 2 months 1,200 questionnaires have been collected in Veszprém city. The computer-assisted data collection (filling one questionnaire required about 35-40 seconds) with the tracking ensure the representability checkable. The data collection aimed at identifying and collecting opinions and attitudes of local residents 16 years old and above, having permanent or temporary address in Veszprém. The sample is representative by age, gender and district (based on an integrated urban development strategy). The aim of the current research is to highlight differences in behavioural patterns and satisfaction among the generations which could be influential in the long-term development of the city which will be the European Capital of Culture 2023. The research results underline the significance of applying the generation theory into regional strategic planning, since dominant differences would be observed how the groups evaluate the environmental conditions, community cohesion of the city, as well as what environmental factors they evaluate as important and to what extent they are attached to the settlement.