If you own only one rental property, maintaining a stable tenancy is usually more important than forcing lease terms to align with a "perfect" expiration date. If you own multiple properties, staggering expiration dates—such as spreading them across spring, summer, and autumn—is generally a safer strategy. You should also verify local regulations regarding lease renewal notices, rent increases, security deposits, and the differences between fixed-term and month-to-month leases; rules can vary by state, city, or even county. In any case, always apply consistent, objective standards to all tenants to avoid discriminatory treatment based on protected characteristics.