OK so I know this is a weird issue and I have found a way to fix it.

Randomly I can no longer open any of the property tools. (Page, Object, Link, etc).

Re-installing VSD does not resolve it. The only way I can fix it is to delete the VSD registry (HKEY_CURRENT_USER\Software\CoffeeCup Software\Visual Site Designer) then re-install.

Which tells me something is getting corrupt.

The question I have is which key is actually controlling the ability to pull up the windows?

VSD 7.0, Build 26
Windows 8.1

Have you tried setting the shortcut for the program to Run as Administrator to see if that fixes the little quirks you're having? If so then please open a ticket with Support so they can help you with this issue. Good Luck!

Already running as administrator.

I will open a support case. thanks