We derive a comprehensive overview of specialization evolution based on analytical results and numerical illustrations. We study the separate and joint evolution of two critical facets of specialization-local adaptation and habitat choice-under different life cycles, modes of density regulation, variance-covariance structures, and trade-off strengths. A particular feature of our analysis is the investigation of arbitrary trade-off functions. We find that local-adaptation evolution qualitatively changes the outcome of habitat-choice evolution under a wide range of conditions. In addition, habitat-choice evolution qualitatively and invariably changes the outcomes of local-adaptation evolution whenever trade-offs are weak. Even weak trade-offs, which favor generalists when habitat choice is fixed, select for specialists once local adaptation and habitat choice are both allowed to evolve. Unless trapped by maladaptive genetic constraints, joint evolution of local adaptation and habitat choice in the models analyzed here thus always leads to specialists, independent of life cycle, density regulation, and trade-off strength, thus raising the bar for evolutionarily sound explanations of generalism. Whether a single specialist or two specialists evolve depends on the life cycle and the mode of density regulation. Finally, we explain why the gradual evolutionary emergence of coexisting specialists requires more restrictive conditions than does their evolutionarily stable maintenance.