Thanks Shawn and Michael, the 5 days is actually with the box checked. So, I looked at the tutorial link that you posted and here's how much space it says.

Used Shadow Copy Storage space: 21.939GB
Allocated Shadow Copy Storage space: 24.063GB
Maximum Shadow Copy Storage space: 69.864GB

I've got 2 HD's one is 250GB and the other is 500GB, but I'm only using System Restore on my C: drive and it has 397GB free so I know I have enough room. By looking at the space that System Restore is using that I posted above, is this why it's deleting them or should is there another reason that doesn't present itself here. I'm just not sure how much room is required to keep older points. Thanks.