The paper discusses why on the one hand William Edmundson thinks that market socialism is superior to property-owning democracy, while on the other hand Alan Thomas thinks that an egalitarian version of property-owning democracy is superior to market socialism. For the purpose of this discussion, the concepts of property-owning democracy and market socialism are systematized and it is argued that those concepts, as understood by Rawls, do not exhaust the list of possible alternatives to capitalism and state socialism. Economic democracy, understood as mandatory workplace democracy, will be introduced as a middle ground, somewhat closer to market socialism than property-owning democracy. Against this background, it is argued that questions of transition and stability are important for deciding between these regimes and the importance of two realistic constraints in making this choice, namely egoism of powerful agents and path-dependency in institutional design, is highlighted.