With the rise of organized houseless encampments or "tent cities" around the U.S., scholars have begun to address the social-spatial effects of encampments on houseless peoples' lives. This scholarship has primarily explained the development of organized encampments as an effect of neoliberal modes of governance as municipalities have sought to offload responsibility for caring for the houseless or to discipline houseless people by containing them through the regulative force of the state. Such explanations address the culpability of the state in relation to capital which shapes houseless peoples' lives. Yet, they leave unaddressed one critical component of houseless encampments: that relations surrounding property ensure that houseless encampment residents remain property-insecure and without a guaranteed right to remain. Through a case study of self-governing houseless encampments in Portland, Oregon, the article advances a relational analysis of property and citizenship to show how self-governing houseless communities are denied key privileges of citizenship that democratic self-governance is intended to realize. In doing so, the case study examines the very tradeoffs houseless encampment residents must make when living in an encampment. The paper ends suggesting that Portland's encampment model allows us to more clearly see the consequences of establishing collective rights to access property within liberal property systems, and from this, where political and scholarly attention ought to be placed to better protect houseless people through a more democratic right to remain.