Check if there is an Oak directory under Local (%appdata%\..\Local vs %appdata%\..\Roaming) and delete that one if it is present.
Hm... that doesn't look very friendly...
I just tried a new login on my system (W10 - renamed the oak folder), and after entering my username and password, it showed my devices, and wrote the config file once I picked one to manage/upload to, that that was v1.0.2 also. So it doesn't appear to be a Particle issue. Are there any funny characters in the oak names (or no names at all?). And am I understanding correctly that oak-cli had worked fine in the past and suddenly stopped working?