Medicaid is expanding funding for tenancy support services (TSS) that help people who have experienced homelessness or lived in institutional settings obtain and maintain housing. To identify critical considerations for Medicaid TSS regulations, we compared two successful TSS provider agencies in North Carolina, and conducted additional stakeholder interviews in North Carolina and Louisiana, which is ahead of North Carolina in expanding Medicaid-funded TSS. Stakeholder concerns focused on the impact of regulation on goals of access, quality, and flexibility, and noted tensions among these goals. Specific regulatory approaches may mitigate the tension among these goals, such as outcome- and client feedback-based accountability, and an emphasis on job-specific training. Moreover, meeting the goals of access, quality, and flexibility and mitigating their trade-offs is supported by state infrastructure that includes braided funding; horizontal and vertical coordination across agencies; and the capacity for multimodal, multilevel quality assurance and multilevel training and technical assistance.