Blitzfx, I'm still on v0.9.3 - I never upgraded to v0.9.4, I didn't see it until Erik rolled it back, so never moved to it. So I only have the one entry for the Oak (Oak by Digistump) on my boards menu. I'm running Arduino IDE v1.6.7, and it seems to be playing with my Oak fine when it wants to behave.
Remember to only have Pin 2 grounded when you want to access the config / restore mode - otherwise that would be the cause of your problems.
That is very peculiar that you are having issues that way - it is programming ok, and is rebooting to load your program, but then gets stuck. Might be worth removing v0.9.4 from your Arduino IDE, and rolling back to v0.9.3 if you can? It doesn't look like the package supports multiple versions, and I don't want to break my working config just yet

, so I don't know if you re-install the oak boards package if it will install v0.9.3 again... I'm just wondering if it is something that broke for your setup when the fast OTA updates function was released in v0.9.4??