The deployment of recently standardized 3GPP New Radio (NR) technology operating in millimeter wave frequency band brings unique challenges to fifth-generation (5G) cellular system design. Particularly, rapid fluctuations of the received signal strength caused by various mobile objects in the channel may frequently lead to outage. The propagation conditions are further complicated when user equipment (UE) is mounted on moving vehicles. To address this issue 3GPP has recently proposed multi-connectivity operation, where UE is allowed to maintain multiple spatially-diverse links to different access points (AP). In this paper, we address one of the most challenging prospective NR deployments - multi-lane street/highway deployment. We show that using the mixture of analytical and simulation modeling one may computationally efficiently characterize the probability of outage in the considered scenario as a function of the degree of multi-connectivity. We then comprehensively study various outage-related metrics including the fraction of time in outage, mean outage time and associated distribution for various environments including normal traffic conditions, traffic jam, highway and emergency scenarios, densities of APs and degrees of multi-connectivity. © 2018 IEEE.