Kieshi I'm not the OP, but I also have the same problem described in the thread when running through the Oculus app, where it gets stuck on 'Loading' when starting DeoVR and never boots up. This only started happening within the last couple of updates and has functioned fine prior to this. The Steam VR version still appears to work fine though.
For reference, I'm using the latest version of the Oculus app (version 60.0.0.162.352) with an Oculus Rift CV1.
When the problem occurs and when looking at the running processes with Task Manager I can see that UnityCrashHandler64.exe is running, but not visible on the desktop. The Event Viewer consistently has an error message similar to the following though which may point to some kind of access violation with UnityPlayer.dll:
Faulting application name: DeoVR.exe, version: 2020.3.42.56850, time stamp: 0x636cce2a
Faulting module name: UnityPlayer.dll, version: 2020.3.42.56850, time stamp: 0x636cce62
Exception code: 0xc0000005
Fault offset: 0x000000000074cabb
Faulting process id: 0x0x64FC
Faulting application start time: 0x0x1DA39DC7897D7F5
Faulting application path: C:\Program Files\Oculus\Software\Software\infomediji-d-o-o-deovr-video-player\DeoVR.exe
Faulting module path: C:\Program Files\Oculus\Software\Software\infomediji-d-o-o-deovr-video-player\UnityPlayer.dll
Report Id: be2b6f74-2a86-4d43-864f-a9d6d2d8b8ca
Faulting package full name:
Faulting package-relative application ID: