Outdoor-to-indoor (OtI) signal propagation further challenges link budgets at millimeter-wave (mmWave). To gain insight into OtI mmWave at 28 GHz, we conducted an extensive measurement campaign consisting of over 2,000 link measurements in West Harlem, New York City, covering seven highly diverse buildings. A path loss model constructed over all links shows an average of 30 dB excess loss over free space at distances beyond 50 m. We find the type of glass to be the dominant factor in OtI loss, with 20 dB observed difference between clustered scenarios with low- and high-loss glass. Other factors, such as difference in floor height, are found to have an impact between 5 - 10 dB. We show that for urban buildings with high-loss glass, OtI data rates up to 400 Mb/s are supported for 90% of indoor users by a base station (BS) up to 49 m away. For buildings with low-loss glass, such as our case study covering multiple classrooms of a public school, data rates over 2.8/1.4 Gb/s are possible from a BS 68/175 m away when a line-of-sight path is available. We expect these results to be useful for the deployment of OtI mmWave networks in dense urban environments and the development of scheduling and beam management algorithms.