I had VSS working well and had accumulated about 40 previous versions of my data directories. After a reboot on Sunday, I lost all the previous versions. The previous versions have now started accumulating normally again. (I am up to 4/2 per day). I do not believe I should lose my previous versions to a reboot.
I didn't just lose old copies to make up for the 64 point limit, I lost all of the copies.
SYSTEM:
Shadow copies are created on a USB drive 465 GB - lots of room.
Windows 2008 R2 server handling the VSS scheduling. Data shares to the users.
Windows 2008R2 virtual machine handling the users via RDP