The paper explores the potential impact of driverless vehicles (DV) on the useful life of structured parking, and options to make them convertible to other land uses, thus extending useful life. However, sustainable investment often involves higher up-front costs to preserve building life and therefore residual value in the long run, and may also require higher maintenance costs and lower cash flows to achieve the same goals. Thus any sustainable benefits from building reuse are essentially eliminated in present value terms, potentially leading to wasteful investment. This paper uses financial simulation modeling to look at the issue in the context of sustainable parking garages, and concludes that under likely future market conditions for parking, developers will be hard pressed to make their required investment returns on new parking structures for holding periods of longer than 10 years on convertible structures, likely leaving the field to the public sector.