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Distribution grid reliability and resilience has become a major topic of concern for utilities and their regulators. In particular, with the increase in severity of extreme events, utilities are considering major investments in distribution grid assets to mitigate the damage of highly impactful outages. Communicating the overall economic and risk-mitigation benefits of these investments to regulators is an important element of the approval process. Today, industry reliability and resilience planning practices are based largely on methods that do not take explicit account of risk. This paper proposes a practical method for identifying optimal combinations of investments in new line segments and storage devices while considering the balance between the risk associated with high impact and low probability (HILP) events and the reliability related to routine failures. We show that this method can be scaled to address large scale networks and demonstrate its benefits using a Target Feeder from the Commonwealth Edison Reliability Program.