Maintenance decisions impact company's costs and profits in various ways. These decisions can be incurred as a part of everyday repairs or heavy replacements or as an investment in future asset or technology. Large corporations with physical assets have maintenance practices to ensure proper operations and to minimize costs. With innovation and development, it is possible to improve the maintenance practices to implement a more effective future technology. These changes may require significant investment decisions, and therefore, it becomes critical for decision-makers to use the best available information with respect to market conditions and potential benefits of every future option under consideration. In this study, condition-based maintenance practice is analyzed in different scenarios, both qualitatively and quantitatively. A strategic maintenance decision for future investment is evaluated using real options approach. The proposed framework is then explored for the airline and trucking industries.