Folders go from shared to not shared after restart

After every restart (usually due to windows update), all the folders on my server go to shared to not shared. It is really starting to get annoying. Especially when using my VPN and need to access an important file but turned out that folder isn't being shared. I am using Windows Server 2008 right now. I will eventually move over to linux when I get the time to learn more about it. Right now Windows Server 2008 is holding steady for me.

 

Another problem I am having is getting the Group Policies going. I am trying to make it so I don't require a password for the guest account I'm working on. So when people use any of my systems, they can just use the guest account to use it without me having to log in all the time. I have changed the password policy and set the minimum requirements to 0 and the complexity disabled. But still can't get past the part of the password without an error stating the password is too short or doesn't need the complexity. I also have that Group Policy Enforced, but it doesn't seem to work right now. My main problem is the shared folders going from shared to not shared