I'm no corporate expert but you know that VSE8.5 and ASE8.5 have been off support for 1 year now so it isn't surprising that there are issues?
End of Support (EOS) December 31, 2011. See KB69579
IMPORTANT: As an exception to the above statement, see KB66079 on support for VSE 8.5i on Windows 2000
I see you are rolling out 8.8 anyway, but thought I'd best point that out in case you weren't aware.