This article reports on our current explorations on systemizable tasks of architectural design and parametric design supported by rule-based generation methods of spatial configuration alternatives to assist user-design processes of progressive development low-cost dwellings. This exploration is part of an ongoing major research towards an integrated planning support system for low-income housing; we called Esther, which is focused on the development of a network-based set of tools to support logistics of self-designed /-built dwellings life-cycle. Esther addresses the systemized collaborative work between dwellers and specialists during the whole development cycle of dwellings.