You should have to activate software once in a virtual machine, because a virtual machine is a different computer from the physical machine it runs on.
Is your Windows installation in a Boot Camp partition, by any chance? If so, it's very important that you allow the installation of VMware Tools during your first boot of your Boot Camp partition as a virtual machine. VMware Tools will help mitigate the activation problem. You'll need to reactivate once more, the first time you boot your virtual machine, and then not again.
Is your copy of Windows OEM-licensed? If so, Microsoft will refuse to activate it on any machine, physical or virtual, other than the computer it was first activated on.
Your Adobe software is demanding reactivation for the same reason that Windows is demanding to be reactivated: it sees itself running on, as far as it can tell, a different computer. VMware Tools does not have any ability to help with this activation problem, it only helps with Windows activation problems in Boot Camp virtual machines.
