I've pushed dozens of OTA updates to WiFi devices (telepresence robots), and it's always terrifying. We'd test thoroughly, and we'd always start with devices in our office, and wait to see them reboot before pushing to customers. In addition, we had a scheme where we'd push an update, it'd reboot, and if it didn't connect to our server within 20 minutes it'd revert to the previous version and reboot again. WCGW? We never bricked one in the field, but I can think of a million ways it could have happened.
The scariest times were pushing updates that affected WiFi connection for customers with unusual network configurations. In particular, we had one with a multi-campus Cisco WiFi system with WPA-Enterprise, which requires logging into a RADIUS server to get WiFi. We were running on FreeBSD which had a half-assed port of the Linux WPA authenticator. We never managed to replicate their network perfectly for in-house testing, so pushing updates to them was always nerve-wracking.