Realizing inclusive development in a city is not an easy matter. The presence or absence of partisanship and goodwill of regional head actors is the main problem. Limited funds and readiness of bureaucratic human resources to serve are other problems because inclusive development requires the readiness of the bureaucracy to work with a service perspective, not just business as usual. This is a serious problem, because most Indonesian bureaucracies work as pangreh praja (local rulers during the Dutch colonial period who guarded their colonies) and not as pamong praja (public servants). The Dutch colonial culture that has been practiced for a long time has become firmly embedded in the Indonesian bureaucracy and it is not easy to change it. Another problem that is no less important is in the community itself, which is not yet capable enough to utilize the participation spaces provided, due to being in a very paternalistic work environment for too long. As a result, it takes a longer time to implement an inclusive policy, because a number of things must be done to facilitate the readiness of the community to be involved. Recognizing the will of the community and finding a common ground (win-win solution) with the availability of government support, another difficult job that must be done. This study tries to explore these things, namely how the Solo City Government under the command of three regional head actors overcomes these problems in two decades of implementing regional autonomy policies in Solo, especially in the context of providing decent housing for the poor. Using qualitative methods and Giddens’ Structuration theory as an analytical tool, these problems can be overcome with two strategies, namely: a cultural approach (Javanese) and a humanist approach; which is also the novelty of this study.