I can only comment on the last screen shot as i have also had the same issues on a new Build to my estate.
If you drop to a command prompt and type DIR /X, Do you see short name details next to the full dir list,
I.e c:\program files and u should also see c:\progra~1.
If not then you have not installed the base image with the old 8.02 format.
Also small note are all your clients not updating the PTP side of the client ?
I had over 300 + clients until i found it !.
Hope this helps u