A system may include a rental property listing portal and a rental price prediction unit. The rental price prediction unit may additional include an amenity price prediction unit. The rental price prediction unit and the amenity price prediction unit may use one or more mathematical models, such as constrained optimization model and/or a machine learning approach such as a random forest model, to generate a suggested rental price at a given level of portfolio occupancy. The system may also provide risk thresholds to simulate leasing strategies based on market situations, predicting revenue potential and possible vacancy for each strategy. The system may also generate a delist time (time to rent) for a property at a given price. The system and method may be implemented in a multi-family apartment rental system, a storage space rental system, a student accommodation, and single family apartment rental systems.