The concept of “smartness” is based on expectation. “Quality of Life” is based on experience. The “learning process” between expectation and experience in Vienna was accompanied by scientific analyses over many decades. They show the chances and the risks – and also the luck – that the city had in the past. In a dynamic city there are always intentions for decisions and projects from the inside and the outside which have to be analysed, whether the outcome will have positive or negative effects on the future development of the city. The future will need more cooperation than competition between cities to keep transport and quality of life in balance not only in the city but also with the surrounding region."br" This paper will give a comprehensive insight into the content of the studies of the processes based on the experience and data from the past, the stability of the existing situation of the urban structure of Vienna city and its internal dynamics, and the outlook into the opportunities and risks of the future of the city, as far as scientific methods allow