With the checkpoints - you need to make it to Windows (safe mode or normal).
The best setup for any computer is a 3 drive system - an OS drive, a data drive and a backup drive. The OS drive is best with an SSD (128GB/250GB) or smaller hard drive (300GB or less), a good data drive (1TB-2TB) and backup drive (2TB-4TB). I create an image of my OS drive, and backup not only my computer - but the rest of the computers on the network using SyncBack Free....
With that setup, if your OS drive corrupts - you can restore the image (you loose programs/updates since the last image was done), reinstall Windows, etc...and never worry about losing your data. The backup drive keeps everything safe.