Experiencing this too. I resetted it once, then it started again. Found a few threads online of GWR owners with the same issue, someone solved it by disabling "ask for PIN" on the watch and "ask for password/fingerprint" on the phone, someone didn't.
I updated some apk (GPS, Android Wear, etc...) by downloading from apkmirror and installing them through adb, but this didn't fix the problem either. In logcat I can see some issues with an intent referring to the Play Store and one with some directories not being read.