Windows 2008 R2 - shadow copy management and retention

1. Yes you can change the limit up to 512 shadow copies per volume, by using the MaxShadowCopies registry key. You will probably also need to adjust the amount of storage space VSS is allowed to use with vssadmin.exe Resize ShadowStorage. (You may configure Shadow Copies for a volume to back up to a separate volume, such as one with more space. Again, vssadmin.exe is your friend here.)

2. No.

3. No.

VSS on its own works well, but it's pretty basic. Most good enterprise backup solutions make use of VSS on Windows machines. But to get those really granular and fine-tuned retention policies, you'll need to use a more thorough backup solution.

My goal is to get to a point where i can have 12 "monthlies" and the previous month twice "dailies" (for a total roughly of 72 copies it would seem).

As you already have noticed, the automatic VSS removal mechanism would always remove the oldest shadow copy/copies and does not allow you to configure a more sophisticated retention scheme. It also seems impossible to set a "no delete" mark on a particular shadow copy set.

To overcome this, you might disable (or at least increase) the space limit for shadow copies and purge them in a periodical script according to your needs by either invoking the diskshadow executable or employing the win32_shadowcopy WMI class. It would be most conveniently called before a new VSS copy is created through the task scheduler of your system.